The birthday comes to a close

Glancing into the rearview mirror Megan took in Bailey sitting in the backseat of the car. Light from the street lamps shimmered across the dark metal surface of the tiara atop her platinum blonde locks. Her makeup was perfect, and it should be considering she had watched Bailey touch up his lips when she had gotten in the car. It was amazing that Bailey had changed so much from her efforts and now did little things like check her makeup without being told. It was impossible for her to see the arrogant twenty five year old man in the person who sat in the back seat wearing another man’s hoodie that was too large and a black dress puffing out from under it. She could see Bailey’s small smile that seemed to be her default expression now as she sat with an otherwise vacant look. Once upon a time Bailey would look like he was contemplating something when quiet, but as Megan looked at the disguised man now it was more of a vacant look. “Well I have to say that was a great party, the only thing Becky would let us do for her eighteenth was take her out to dinner. You looked like you had a great deal of fun Bailey.” Looking over at Aunt Megan in the driver’s seat, Bailey could see the friendly smile of Mandy looking back at him expectantly. “Oh like I had the most amazing time.” Bailey reached up and touched his ear nervously, feeling one of the earrings that dangled there.

Reaching into the back seat Amanda took Bailey’s hand that was mostly covered by the long sleeve of the hoodie. She tried to give a reassuring smile as she thought about this person being her daughter, boyfriend or ex-boyfriend all at the same time and squeezed Bailey’s hand a little. “You looked like you had fun, but was it actually that much fun for you?” Bailey enjoyed feeling her long slender fingers on his, even if her hands were cold. He remembered once pulling his hand away from her when he felt her cold hands and regretted it now. He regretted complaining that she would put her cold feet on him in bed at night and wished he still shared a bed with the woman he loved. His eyes flicked over to the driver, seeing her blue eyes gaze at him from the mirror and amped up his smile. “Mommy.” Bailey took a hold of her hand into both of his and lowered his head a little as he leaned closer to the front seat. “I had a blast, it might have been my best birthday ever.” It was definitely the most emotional one he had ever had, but a glass of expensive whiskey and a blow job from her was a pretty good birthday too. It really did feel good to have people come to celebrate and really take their time with personalized gifts, like getting to see Cherry again. It seemed like that answer was the one she was looking for and he wondered if this was a test to stay in character or if he had missed a chance to actually speak his mind, not that it was much of an option with Aunt Megan around. Though he did wonder if he could sleep in the same bed as Mommy again and figured it wouldn’t hurt to ask as soon as the wicked witch of the west was gone.

Amanda was still holding Bailey’s hand and was incredibly happy Bailey had such a wonderful day being able to relive part of a childhood he didn’t have growing up, when her sister chimed in confusing her. “Today was a full day, but did you have a chance to do your homework Bailey?” Letting go of Bailey’s hand, Amanda shifted in her seat to look at her sister. Catching the look Megan glanced at Amanda before looking back to the road. “We came up with an idea to help Bailey fit in more as a teen high school girl. What adult remember the pythagorean theorem, but high schoolers would. Bailey what is the pythagorean theorem?” Bailey looked up at the ceiling of the SUV and thought back to the workbook he had been doing. “Ahh its like about triangles where you multiply the shorter sides together to get the longer side.” Megan glanced back to her younger sister. “See? She knows thanks to her homework. You didn’t answer my question Bailey. Did you do your workbook today?” Bailey shook his head, wondering when he would have had time and recalled he hadn’t done his ballerina practice either and hoped she forgot. “Hmm are you sure that is right?” Amanda said, the formula didn’t sound accurate. “I have no idea, and that is why I have your daughter doing some school work for things she should know.” Amanda nodded, agreeing with the statement. She looked back at Bailey raising an eyebrow waiting for the answer to the question. “Are you going to answer your Aunt?” Letting out a sigh Bailey huffed. “No I didn’t and I already answered.” Amanda looked back forward and shook her head. “No need to get an attitude, no one can hear you shake or nod your head. It might be best if you did a page or two before you went to bed tonight.” Amanda smiled at her big sister for a moment, happy she had asked her for help with Bailey with her experience raising Becky.

Getting back inside the two bedroom apartment Amanda and Megan helped get the gifts and other things from the party into Bailey’s bedroom. The balloons floated up to the ceiling and Bailey knew he would be falling asleep after seeing the number eighteen balloons. Once in his room Bailey kicked up the incredibly high heels and flexed his toes in the carpet. “Oh that feels so much better.” Amanda cocked her head to the side and smiled a bit in amusement, it hadn’t occurred to her how Bailey had not taken off her heels all evening. Poor girl is learning the hard way that she can’t wear... She glanced down at the heels again, maybe six inch heels with an inch platform without some pain. “Okay, time to get ready for bed. You get changed and I will be back to brush out your hair.” She was about to leave the room when Megan walked in carrying a little white paper bag that Bailey recognized as the one given to him at the doctor's office earlier that day. He had left it on the kitchen table in his rush to get ready for the party. “What is that, I don’t remember anyone giving Bailey something in a white paper bag?” Megan sat on the bed, dumped out its contents, the jar of cream, the dick looking applicator, a small vial and a small bag of needles and lastly a printed set of instructions. Bailey’s eyes locked onto the phallic dildo applicator and wished he could have hid it before it was seen. Stepping forward Amanda picked up the piece of paper and glanced over it and flipped to the next page. “Ah, this is about the prosthetic you got earlier today.” Amanda said without looking up, when she flipped to the third page she looked at Bailey with wide eyes. “Oh my god, that is right you have a different anatomy right now. I had completely forgotten, sweetheart go ahead and get undressed so I can see.” Megan reached over and tugged the papers from her sister's hand.

“Did you just say oh my god and go on about how you had a blonde moment? Well I guess we can see where Bailey picked up being an airhead from.” Amanda glared at her sister who was already ignoring her and looking through the paperwork. Bailey hadn’t moved, he had stopped thinking about how his groin felt. Though as they brought it up and asked him to strip he could feel his manhood inside the gel-like substance, trapped inside a fake pussy. “Say, this says you need to have an injection every month to help with your hormones. Did you or April do that today?” Megan said, putting down the paperwork and picking up the small vial of liquid. “Ahh no.” Bailey said completely forgetting about the injection the doctor gave him so many hours ago. “Sweetheart, take off your sweater and dress and I will do it for you. We cannot have you playing games with your health if the doctor said you needed this.” Bailey opened and closed his mouth a few times before nodding and undoing the toggles on the warm fleece hoodie. “You mean her boyfriend’s sweater.” Megan corrected while opening up the package of disposable needles. “Just because April teases us about her becoming Bailey Ann Gates doesn’t mean you need to start in on it too. They are hardly dating, right sweetie?” His cheeks flushed right away and it suddenly became harder to unclasp the toggles. Of course they weren’t dating, he was another man! A man that he had tasted the cum of and had little choice thanks to Miss April to do again. “NO…! I do not have a boyfriend!” Bailey said pulling off the jacket and tossing the thing to the floor. An idea struck Bailey about the upcoming date where the boys wanted to just chill and watch Netflix and he was sure to do other things. “Ah.. Mommy, later this week, like Thursday night. Candi wanted to double date again with the boys and ahh umm watch a movie here or at Candi’s hotel. Do you think, maybe you could tell me no?”

Pursing her lips Amanda thought as she motioned for Bailey to spin around and when she complied Amanda pulled down the zipper on the dress. Making sure to take it and put it on a hanger, unlike the sweater Bailey had tossed to the floor. “Are you sure it would be wise to cancel? You have already been out with August on a date before, it might look odd you not wanting to spend time with him after you danced with him so much tonight and he gave you his jacket.” Closing the closet door after hanging up the dress, Amanda looked back at her sister and put her index finger to her chin. “I have to agree, it would look suspicious, but you will not be able to do it at the hotel. Derrick has to fly back to California tomorrow.” Amanda was going to continue, but Bailey rushed forward wearing only a bra, panties and the tiara before wrapping his arms around her. “Really! They are going back!” Running her fingers through Bailey’s hair Amanda looked into Bailey’s green eyes with concern. “It will just be Derrick and only for the rest of the week, he has some things he has to do in order for him to stay for the summer.” She looked into his green eyes longer, it was much different now with the long thick lashes and makeup and thought it best to bring up the conversation about ending this now instead of waiting for the weekend.

“Bailey honey, if I gave you the option for all of this to end this weekend, would you take it? Forget about my job, just think about you and me.” Bailey felt speechless, that would be amazing, it would be incredible, it would be something he didn’t even dare to wish for! He wanted to yell yes, a thousand times yes! Still holding onto the woman he loved, feeling her breasts press into his own swollen chest he was so happy she asked, but then he looked over at the Wicked Witch sitting on the bed who sat on the edge looking like the cat that ate the canary. If he spoke his mind what would she do? Fuck if he agreed what would happen with the police? This was incredibly not fair! If he opened up and told her the truth of how he felt, but how he had to keep this going because of the cops, what would she say? What would the Witch do? Would she even continue on with the private investigator? There were just too many unknowns. It hurt him to do this, but he just didn’t see another way, god he wished he did. Stepping back from the embrace Bailey shook his head, pulling the tiara from atop his head when he felt it shift. Bailey looked down at the dark metal and steadied himself mentally and unfortunately looked like he was reflecting on the night as he looked at it. “I like can’t do that to you Mommy, you will get what you deserve.” Behind Amanda’s back Bailey could see Megan rolling her finger in the air for him to keep going. He wasn’t sure what more to say and glanced around the room that had been decorated just for him, Bailey Ann Best. His eyes stopped on the hair brush, and remembered her humming a tune happily as she brushed his hair. “Aren’t you enjoying having a daughter?” Sugar! He kicked himself that was too far, he should have said it wasn’t so bad. Amanda’s eyes welled up and hugged Bailey, he wasn’t expecting it and she pinned his arms to his sides and she rocked him in her arms in the embrace.

“That was sweet, but it is getting late and Bailey has a few things to do tonight.” Amanda pulled back, biting her lower lip as she smiled at Bailey. She reached forward and put her hand on his cheek before pinching it lightly. “Yes, first we need to get you to take your medicine. Turn around and bend over for me sweetheart.” The hug was over too quickly, she loved what he had said and he had hated it. Sugar, sugar, sugar! Bailey’s mind screamed as he did as instructed. It was surreal to be standing here like this wearing girls underwear while bending over and Mom... Mandy injected him with the medication from the doctor. He didn’t understand why he needed an injection for a prosthetic, but maybe it was so his dick didn’t wither away under the thing. “Ow!” Bailey cried out when he felt the needle sink into the meat of his ass cheek, Amanda gave his ass cheek a playful slap. “It wasn’t bad, don’t be a baby. Now finish getting undressed.” Bailey rubbed his butt where he was injected and smacked before reaching behind him and unclasping his bra, while Amanda busied herself by stepping over to Bailey’s white dresser and opening up one of the drawers. Next Bailey put his thumbs into the elastic waistband of his panties and couldn’t believe he was thinking of the female garments as his, let alone about to pull them down to show off his new female anatomy. Fully naked Bailey tried to brace himself mentally as Amanda turned around to see him. He couldn’t help but frown when he saw what she had grabbed for clothes, she was holding a pink thong lace waisted panties in one hand and the other a black silk babydoll nighty with pink around the breasts and hem. “You really are running out of clothes…” Amanda stopped and took in the sight of Bailey fully nude in front of her, her jaw hanging open.

Bailey stood there with his arms behind his back, one hand gripping the other forearm, one foot turned to the side on the ball of his foot. Bailey’s head was to the side and looking down, causing the platinum hair to cover part of her face. If it wasn’t for the obvious discomfort it would look like she was posing. Her eyes looked between Bailey’s legs and saw what she would expect if Bailey really was her daughter. It was astounding, some part of her still expected to see his penis hanging there and instead it looked like a freshly shaved vagina. Her eyes moved up Bailey’s body, noticing maybe for the first time how much weight had been shed recently and then her eyes stopped at Bailey’s chest. The breast forms were gone, or somehow Bailey got a hold of a smaller pair. She wondered briefly how she hadn’t noticed Bailey having a smaller chest and when her eyes flicked to the discarded bra on the floor she could see a few small flesh colored items that girls used to enhance their appearance. Reaching forward Amanda was about to put her hand on Bailey’s chest when he pulled away. “Please don’t, they are sore.” Her senses coming more back to her as she recovered from the shock, Amanda swallowed still examining the whole of Bailey. “Honey… Why do you have breasts?” Bailey covered his chest with one of his arms, feeling extremely exposed. “I don’t have breasts! It is just a reaction from the glue that was on my chest for multiple days and sweat.” Pursing her lips Amanda shook her head slowly, positive at what she was seeing. “Amanda, if there was something to be concerned about, don't you think the doctor would have said something today? Unless the shot you just gave was to sort that out” Megan moved her focus to the still naked Bailey. “Did the doctor today say anything about your chest?”

Bailey thought back to the old balding doctor as he moved the dildo into the new opening between his legs. “Ahh, no.” Amanda looked harder at Bailey till she caught his eye. “Did he see your chest?” It felt like she was interrogating him like a child that was lying about eating the last of the cookies. “He did and ahh… Angela, I mean the nurse measured my chest.” Bailey thought about how he had gotten hard from her touching him. “Well, if he was aware then I guess everything is okay.” Amanda said with apprehension in her voice and handed Bailey over the clothes she had in hand. The clothes felt like something he would rather hand her to put on as sexy as they were and really wished he had his wallet to buy some regular pajamas. Bailey started to get dressed and Amanda was about to leave the room to get ready for bed herself when Megan spoke up again while reading the paperwork from the doctor that she had only glanced at. “It says here you have to apply the cream and use the applicator on the prosthetic at least every other day.” She pointed to the line for her sister to read and then picked up the jar and provided dildo. Bailey looked at Aunt Megan sadly and shook his head just a fraction. “No…” Megan held the objects out to Bailey with a stern look. “I know you are tired, but as your Mom said before. You have to follow the doctor's orders.” With great **** Bailey moved over to sit on the bed next to the wicked woman and took the objects she was offering. Amanda read the section about the maintenance and then looked back to Bailey. “Yeah honey you are going to have to do that or it could dry out, or even close up.”

The paperwork described what had to be done and said to use the applicator, but the object was clearly a dildo. “When you aren’t using that, best to put it somewhere that no one will see it.” Amanda opened the night stand next to Bailey’s bed and inside saw the little pink book that she had seen Bailey writing in and a purple dildo. She shut the drawer and gave a small smile to the two others. “I’m going to go get changed, unless you need help?” She looked at Bailey with **** in her voice. Bailey quickly shook his head thinking about her fucking him with a dildo. “I will be right here if she needs anything, you go take care of yourself.” Amanda put her hand briefly on her sister's shoulder and left the room, not wanting to think about what Bailey was about to do or about what she saw in the drawer. She would have helped if she needed, but it felt wrong on a few levels. It was medical, but felt sexual and she really had never been attracted to woman and like it would be an invasion of Bailey’s privacy. The object she saw in the drawer probably had an explanation, like Megan gave it to her because what teenage girl wouldn’t have something like that.

Getting up Megan closed the door behind Amanda and smiled at Bailey. Alright birthday girl, are you ready to use that thing?” Bailey frowned at the thing in his hand and felt disgusted. “Oh I have an excellent idea!” She said picking up Bailey’s phone from the vanity. “You are still wearing your makeup, so why not take a shot with your new toy for your boyfriend Auggy?” Bailey pinched his face and glared at the woman. “Auggy? What… no and he isn’t my boyfriend.” Megan wagged her finger at Bailey. “You are forgetting yourself Bailey, what does a good girl do?” Bailey held his frown firmly for a second before changing it to a smile. “A good girl always looks her best. A good girl is polite. A good girl is always obedient. A good girl always smiles. A good girl is seen and not heard. A good girl never argues or complains. A good girl never uses foul language. I am a good girl, happy and proud.” Megan gave a small quite clap. “An obedient girl would do what she was told and a good girl wouldn’t argue with me would she?” Bailey kept the smile on his face and shook his head just a fraction, hating to agree with her. “Then be a good girl for your Auntie.” She said holding up the phone ready to take a photo. Tilting his head to the side just slightly Bailey touched the dildo applicator thing to his cheek at an angle so it was just to the side and up a little from his mouth, while trying to give a shy smile. His eyes were looking to the side toward the phallic object and held that pose for her to get the horrible photo over with. It was the type of pose that he could see himself jerking off too and knew if he didn’t do something good enough Aunt Megan would make him do multiple poses and the worst one he could think of would be with his panties off, legs spread and holding the dildo like he was about to use it and did not want a photo like that to ever be taken. Megan took the photo and sent it as a text to young August.

Bailey: I named it August so I can think of you when I use it.

Bailey: Hope that is ok ;-)

August: That is more than ok!

August: Damn wish I was there.

Bailey: Auggy, that would be wonderful, but I don’t think Mommy would like that.

August: Yeah, I’m a full grown adult and I bet my Mom would make me keep the door open still if I brought any girl over.

August: I really need to move up from an intern so I can afford to move out.

Bailey: Any girl over? Are you dating more than just me?

August: Ummm, Honestly Bailey I have only dated one other girl before you. So, no. Only you.

Bailey: Hmm, k but like what would you do if I dated others

August: Do my best to make you forget about them and fall head over heels in love with me.

Bailey: Hmmm I totes like the sound of that <3

“Your boyfriend loved the photo and you calling him Auggy, I think it is cute. Now you have put this off long enough to text your boyfriend.” Bailey’s mask faltered for just a second with her having the gall to say that when she literally had his phone in her hand. He looked up at her standing there as she raised an eyebrow as if to ask what he was waiting for. Closing his eyes Bailey took a deep breath before standing to shimmy the panties down. Not having a piece of fabric between his ass cheeks would have been nice if he didn’t now of to stick something inside of him… well kinda in him. Sitting back down, Bailey opened his legs and moved the dildo to the lips of his vagina. “Not yet you silly girl, you are in such a hurry that you forgot to use the cream.” Bailey looked down at his hand between his legs ready to penetrate himself and whimpered before putting it down to open the jar of cream. The white substance felt like a mixture between hand lotion and a gel and as he spread it over the phallic object it got clearer as it was spread out, leaving the dildo looking like it was glistening in the light of the room. Starting again Bailey lined up the thing once more and pushed in slowly, tensing his body like it was going to hurt. He of course couldn’t really feel much at all, while the prosthetic looked and felt real it was not his skin and had no nerves for sense of touch. The most he felt was the pressure as it pushed against his own trapped member. Moving it slowly he pushed it back as far as it would go, the vaginal cavity wasn’t deep enough to take the full dick and just sliding it in caused almost no stimulation. “You are never going to get off that way sweetheart, here let me show you.

Megan was still dressed up for the night minus her heels that she had kicked off at the front door. Crawling onto the bed she sat behind Bailey with her legs spread around him and pulled herself up close enough that Bailey was leaning back against her large bosom. She reached around Bailey who seemed to have frozen like a deer in headlights. She could see them both in the vanity mirror on the wall next to the bed. She wrapped one hand around Bailey’s right hand that held the dildo and moved the other to the wrist of Bailey’s left hand. Megan moved Bailey’s left hand to the feminized man’s chest. “With this hand gently squeeze your breast, and roll your thumb over your nipple through your lingerie. Come on, you can do it.” Her words were soft and encouraging. It wasn’t lost on Bailey he could look forward and see what was happening and as he did what she said he felt a small jolt of pleasure from his chest, much like that morning with the nurse. “That’s it, keep doing that with your left hand.” With her right hand she squeezed Bailey’s and gently pulled the dildo back so that it was almost out and then pushed it in about half an inch before pulling it back again. “Nice and slow, nice and slow. Every couple of pushes you go a little deeper.and then a little more. You can twist it a little as you push in, yeah that feels good doesn’t it babygirl.” Between his chest and what she was doing or making him do Bailey’s breathing had changed as he got more and more turned on. His cock had come to life, trying to expand, making his groin feel more trapped. The enlarging penis caused the vaginal tunnel to grow tighter and that meant as he pushed the dildo in it caused more friction as it rubbed over his hidden cock. This went on for a few minutes when Megan, still behind him, gave a kiss to his cheek and pulled away. “You can stop now if you like.” Watching that had left her feeling wet and didn’t think it wise to continue.

Bailey didn’t want to stop, he hated that he didn’t want to stop. Feeling what he was feeling and seeing what he was seeing was better than porn, but there was no way he was going to keep doing this while she looked on. An audible slurp could be heard as Bailey pulled the dildo free from himself. His hidden dick was still hard as were his nipples as he sat there wide eyed looking at himself trying to regain control of his breathing. Megan pulled a tissue from a box on the vanity and handed it over. “Best clean that off before you put it away dear.” Numbly Bailey did as she said and as he opened the drawer on his night stand to put it away he looked at the contents. His diary and now two dildos, Bailey sighed and then it hit him that Mommy had looked in this drawer, he quickly turned to Aunt Megan with the object still in hand. “Oh my god, like, like… she ahh… Mommy, she.. Saw the dildo you gave me!” Megan put her hand on each side of Bailey’s face and gave him a small smile. “She didn’t say anything, did she? I doubt she was even paying attention, put such thoughts out of your mind baby.” Bailey felt her give him a kiss to his forehead before moving away from him and putting the jar of cream in the night stand drawer before taking the applicator and putting it away with it. Bailey nodded to himself trying to convince himself she was right. Of course she would have said something if she suddenly saw her boyfriend with a dildo, why wouldn’t she? Okay, okay. Bailey smiled a genuine smile at Aunt Megan. “Thank you.” She looked at him with a sad smile. “Don’t thank me yet young lady, you forgot to do your homework and ballerina practice today. So tomorrow you do two extra reps on the stairs and spend some time with your feet under the couch, pulling your feet forward like you did at my house. Now put your panties back on, and go out to the table to do your homework. Unless you rather me think of a different punishment?” Bailey shook his head and hurried to put on the panties. It was odd to not have to tuck himself away and not see a bulge, not that the thong would hide much and damn he hated the feeling of them between his cheeks, but didn’t stop moving once they were on and was out the bedroom door.

Sitting at the table Bailey wrote in the book Aunt Megan had made, flipping to the back for the answer key when he was finished and then going back and erasing his word and starting again to try and do the problem right to be able to get to the right answer. Having the answer would be fine and he could just copy that over, but she had given strict orders that he had to show all his work. While Bailey concentrated on high school math that should be easy for him, Amanda got herself and her sister some coffing talking a little, before realizing she had only told Bailey part of what was going to go on this week. She was hesitant to interrupt her with how much she was concentrating on it, with how much she was using the eraser Amanda guessed Bailey was having a difficult time with it. Still Bailey needed to know and she went into how Candi was going to spend the rest of the week with them and sleep on the couch till Derrick got back Thursday night or Friday morning. “That sounds wonderful Mommy, it will be like a slumber party.” Bailey had said thinking about how what little privacy he did have would go away for the next few days. He didn’t want to dwell on it too much, he was exhausted and turned on with no real way to take care of it. So he tried to buckle down on the infuriating math. He was good at math, always had been and yet he got almost every answer wrong the first time he tried, but he guessed almost every was an improvement from every answer like before. Bailey gave a wide toothy grin, holding up the workbook and pointing to a question. “I got it right!” He was proud of himself for getting it right on the first try unlike the last four problems.

“That is good to hear pumpkin.” Amanda said not looking at the page, but still smiling back at Bailey who had a wide grin on her face. That is something she had really loved about Bailey lately, she constantly was smiling and it was a wonderful change. She was so proud of Bailey with everything that had happened, she had even given her a chance to scrap all this, but she pushed on. Seeing Bailey without any clothes surprised her and she wasn’t really sure what to think about all of it, but if the doctor hadn’t thought there was a problem, who was she to judge? It would be like her telling Bailey about an expense report and Bailey second guessing her. Amanda smiled looking at Bailey who had a slightly checked on pencil between her teeth as she flipped to the back of her workbook to check another answer. “Be right back.” She said getting up and heading into Bailey’s room to get her brush. Coming up behind Bailey she started to run the brush through Bailey’s platinum blonde hair, humming happily. “Mommy… I’m trying to do something. You are going to make me fall asleep.” Bailey whined as he had to erase the answer to another problem. “Hush dear.” Amanda said giving a wink to her older sister, who was enjoying the last of her coffee. The brushing felt so good, and Bailey closed his heavy eyes. He knew he couldn’t fall asleep, he still hadn’t cleaned off his makeup or moisturized and still needed to finish this page, so that he could avoid being punished. He could close his eyes for a minute or two while she ran the brush through his hair though, it wouldn’t hurt. He thought as the humming seemed to get further and further away and he slipped off to sleep, still sitting in the chair with the eraser in hand.