Nana Connors

The lollipop spun around between Bailey’s fingers as he sat back in the car with April. He didn’t want to talk, not to April… not to anyone. His groin felt weird, much different than the tuck kit. Before his tick was just between his legs and balls pushed up, now.. Well his balls were the same, but his dick was pulled back and enclosed in some sort of gel. He could easily twitch his member if he wanted, but it just felt odd. The feeling itself wasn’t what kept him from saying things, it was the idea that he wouldn’t be able to see his own dick for at least two weeks. No matter how horrible things were through this so far he could always look and feel himself to know the truth, that he was a man. While he hadn’t gotten a good look at his now female looking genitalia, he knew that moment was going to hit him hard. “Now that you are done with your gynecologist appointment we have more errands to run. Your mother doesn’t often have me go and do things like pick up dry cleaning, but today is a special day. We will be picking up some dry cleaning, picking up a new dress for you.” April stopped talking as she saw Bailey look up from fiddling with the candy. “I thought that might get your attention, I helped pick it out and I’m sure you will love it, Auntie April has great taste.”

“Auntie April?” Were the first words Bailey had said since leaving the doctors. “Miss April makes me feel like a school teacher, besides your Mom and I have been friends for years. I know I call my Mom’s best friend Auntie. That means I have known you since you were a pretreen at least, and with me set up for guardianship over you if something were ever to happen to your Mom. I’m not the type to make you say how happy you are to have me as an Aunt, but I do expect you to address me as such.” She saw Bailey’s scowl, but noted that he didn’t even bother to open his mouth in protest. “After we pick up your dress, we will be picking up your best friend before we head to the airport to pick up her Grandmother. Mr. Connors asked me to pick her up, she is flying in for her birthday party as a surprise and he has a few meetings he couldn’t get away from.” Bailey rolled his eyes, not at the idea of the man being busy, but for two reasons. The first just the mention of the man, the very idea of him and that as big as she was acting, April was just a glorified errand woman. “I bet you are excited to see your new dress after you asked me to take you shopping earlier.” When no reply came April looked over to the apparent blonde teen in the car with her. When she did Bailey made eye contact only for a second, but when they did Bailey pulled off the wrapper for the lollipop and put it in his mouth.

The pair rode in mostly silence for a few minutes before April turned the radio on to NPR radio. “Gah..” Bailey said as he heard the talk radio start and pulled out his cell phone. Seeing messages from August on his phone made him feel what he imagined was the opposite of what a girl would feel. Still he pulled open his text messages knowing between Aunt Megan and April he really didn’t have much choice and he truly didn’t want Aunt Megan to start texting as him again.

August: You and my sister spending some time together huh?

August: It brings me joy you thought of me, and I can promise I think of you often.

August: Say, is she playing hooky today? That isn’t much like her though it would do her good

August: Do me a favor and see if you can get her to loosen up today she has been so uptight about some secret.

Bailey: Do what I can

She is uptight about a secret!? I have to live it and it is smothering me… part of me literally now. Bailey thought as he gave the younger man a confirmation he would do what he could to cheer her up, not that he had any intention of following through. Sitting sullenly Bailey tried to keep himself occupied by looking out the windows and paying at little attention to NPR. It was obvious Bailey was mentally checked out to April, but she couldn’t help but notice how Bailey played with his hair or spun the lollipop around in his mouth, looking much like the teen girl to anyone looking. Before they got to their destination a call came through the car’s speakers, interrupting the radio broadcast. “Hey April, I just wanted to check in to see how everything is going. Did that appointment with the study go well for Bailey?” The sound of Amanda’s voice pulled Bailey back to the present. “She is here right now, Bailey what do you have to say?” Bailey pulled the sucker from his mouth, upset that the woman he loved knew about what had happened to him. “Mommy do you know like, what they did to me!?” There was a pause on the other end of the call before Amanda responded. “I do not know the specifics honey, April said you were going to get a prosthetic like the fake breasts. Why did they do something else?” Bailey thought about the dildo inside of him and the feeling of cumming. The image of the dildo slick with whatever cream was on it an his own cum burned into his mind from the shame and had no intention of telling her about it if she didn’t already know. “Ah, umm.. No it's just like different.” Bailey fidgeted with the mostly gone piece of candy in his hand. “I know baby, but you know this is for the best. We are both lucky April found this, just think what would happen if someone saw you with your panties down. April, thank you again. I do not know what I would do without a friend like you.” Bailey rolled his eyes thinking how things could be better without her at this moment. “Yeah Aunt April is a lot of help.” Amanda had no way to get the full context with the eye roll and laughed. “Oh I love that! She is kind of like an Aunt to you, April is it okay if Bailey calls you her Aunt? You have felt like family to me for so long, that just feels right.” With a grin full of mischief she looked over at Bailey. “It would be an honor, and I agree. Amanda you have felt more like a big sister to me for years.”

The horrible thought that it would get out that it was his idea to call her that didn’t sit well and he knew he could easily give her back the credit, saying she was just modest and it was her idea. Though when he went to do so Amanda said she was in a hurry, and only had a few seconds to chat and loved them both before handing up. “Getting a random call from your Mom to check on you and say she loves you. Honestly I’m a little jealous, I wish my Mom did things like that when I was younger. Most of the time it is her just waiting for me to call and then asking me why I hadn’t done it sooner. You, my niece are one lucky girl.” Bailey wanted to tell her to go fuck herself, but the only thing that came out was something much sweeter. “Oh, Sugar!” Before he returned his attention back to the window to see the shopping plaza they were turning into. The stop at the dry cleaners was quick and Bailey waited in the car and cared little that April, his tormentor for the day was taking another phone call as she hung the clothes in the back seat on a hook. It did surprise him when she came around to his door and opened it after hanging up the phone. “Out of the car missy.” Bailey scowled at her, but complied. “The dress shop is in this same plaza, I’m guessing your Mom stopped in when she dropped off the clothes and got something for you, but before we go any further.” She paused holding a hand in front of Bailey to make sure he didn’t walk away. “I have seen that scowl more than once today and if you want to be a little moody brat that is your right as a teen girl, but I thought you had a pledge or something about being a good girl. Tell me what that is.” Of course she freakin knew about that, why wouldn’t she, Bailey was thinking. He didn’t have to decide if he was going to tell her or not as he started to recite the mantra right away without thinking about it. “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.” Bailey was angry at himself, his mouth betraying him, while April seethed a little on the inside at the horrible saying. “Well I know for a fact you have not been following that, is that just something you say or something you do?”

Bailey hung his head and felt like crying as he bottled up his emotions. He didn’t want to say any of that, he didn’t want to act out any of that, he didn’t want to look this way. He wanted to shout at her, yell about how she was being such a bi… not nice to him, but she knew about what he did with her brother. That information could not work its way back to anyone and didn’t want to dare give her a reason. “It's like who I am.” April crossed her arms at the disguised man, not sure why he would come up with such bullshit except to say that is how he wanted girls to act and him saying it was who he… she was, but not act it was just confirmation. “Then smile, go inside that shop there and tell the person behind the counter how your Mom bought you a dress and you can’t wait to see it. Then if you want me to I can take a video of you holding it against yourself and thanking her for it.” Those large dark eyes of hers were hard and he knew it was a command. The reminder of the motto already had him giving her a pretty smile. He walked around her hearing the click, clack of the heels he wore. Hating the sound that he once found so sexy, hating the sway of his hips and thinking how a video like that wouldn’t hurt his reputation or his ego. That he hated the most, that catching him on film acting like that would just be considered his current normal. Telling the middle aged man about the dress, holding the dress to him and thanking the woman he loved for it while blowing her a kiss was easier, much easier than he would have liked. After the shop worker folded the dress up and put it in a thin rectangle box with a bow, he left the shop with what looked like a happy April. At least I succeeded in the task from August he thought sarcastically.

When Bailey put the box in the trunk of the car April gave Bailey a side hug. “That was incredibly cute and I know that made Amanda happy. I’m sure she would have liked to be here with you, but she works hard and I think all of us want to make sure that goes as smoothly as possible right now. With that in mind time for our next errand and it is not to pick up your friend like we planned. Mr. Connors called to let me know his mother’s flight is ahead of schedule, so we are going to pick her up first and then I’m going to drop her and you off back at their hotel.” April saw the question already forming and answered it before it could be asked. “You can get ready there for tonight, I have a lot more to do for the party tonight and can’t babysit you. Mrs. Connors will have to do that.” The entire car ride to the airport Bailey just kept repeating the word Babysit over and over in his mind, what eighteen year old needed babysitting! He had been fine on his own for years and it wasn’t like he was going to order an escort, not looking like this! Not, not with his manhood locked away behind this extra layer of fake flesh. His own mind crew quieter and quieter with its thoughts. He didn’t want to argue with her, he just wanted to curl under his comforter and go to sleep.

Seeing the line for pickup April let Mr. Connors know they would be parking and walking in to meet his Mom or they might be waiting here for over an hour. Bailey was standing next to April in the airport hoping she knew what the old hag looked like or if she was foolish enough to think she could just spot her not knowing and not having a sign with her name. When he saw her Bailey knew he was dead wrong, there was no way he could mistake the elderly lady for anyone other than his friend’s grandma. She looked like a shorter and much older version of Candi, but with brown hair that has mostly all greyed over through the years. She wore black slacks, a charcoal grey button up blouse, on her feet were a pair of low heeled shoes. Her tired eyes seemed to gain more life as she looked at Bailey. He knew he shouldn’t have thought of her as a hag, she looked kind… she looked like Candi. Stepping closer to her Bailey smiled and gave a little wave mostly with his fingers at her. “Mrs. Connors, it is a pleasure to meet you.” Bailey said being polite and feeling a little guilty, he had been having a bad day and thought the worst of someone he hadn’t even met. The elderly woman’s gloved hand reached out and lightly pinched Bailey’s cheek, catching by complete surprise. “Candace dear, you have grown into such a lovely young woman. It is a pleasure to see you too I suppose.” She laughed a small chuckle at using the same word back to the young blonde. Bailey looked over at April who was held her hand over her mouth to keep from showing her smile, or to hold in a laugh. She was of no help so Bailey shook his head. “No Mrs. Connors, you are not my grandmother, I’m not Candi.” The elderly woman gave a warm smile that actually reminded Bailey more of Derrick. “I’m not so old that I can’t recognize my own granddaughter, you will have to come up with something better than that. Now help me with my bags and if you are good maybe you can unwrap your present before your party tonight.” Bailey shook his head again and took one of her hands into both of his to try and make her understand.

“My name is Bailey, I’m not Candance, we are not family.” He said the worse sweetly and slowly, but instead of understanding coming to her face she hardened her expression and pulled her hand away. “That isn’t funny young lady, I have had quite enough of this game. My little Derrick was full of mischief and rebellion and I never thought you would act in such a way. Enough of this, I have had a long day.” Bailey’s smile fell, he was not going to have some other misunderstanding happen, he could only see this growing out of control to keep her happy. He imagined Candi pleading with him to pretend to be her just while she is around and Derrick requesting the same. Saying how she is old and how with her stubborn side she would make everyone's life miserable if she thought people were playing her for a fool. “Listen to me! I am not Candi!” Bailey was going to continue when the old woman’s gloved hand touched his cheek for the second time since he met her, but this time it was when she slapped him across the face. “Birthday girl or not, you will not take that tone with me! If you would rather go find a switch when we get to your hotel than have a birthday present we can arrange that. Now grab my bag Candance before I truly get cross with you.” That was when April strolled forward and took the handle of the large rolling bag. “Hello Mrs. Connors, my name is April Gates. I believe your son told you I would be picking you, why don’t I take your bag.” The elderly woman let out some air from her nose and smiled to April like she had to Bailey just a few moments ago. “Nice to meet you Miss Gates, you can call me Edna if you wish. Thank you, I’m glad someone here has some manners.” April looked at Bailey who held his own hand to his cheek, looking shocked to have been hit. “She does too, but teenagers like to push their limits and please call me April.”

Back in the car Bailey had to sit in the back seat while April and grandma Connors talked. Bailey pulled out his phone and texted Candi.

Bailey: I’m sorry.. I promise we can go do whatever you want, but you have to help me!

Candi: Well if we can do whatever I want then I guess I can take a request or two from my little sister.

Bailey: You know how we were going to pick up your grandma together?

Candi: Wait.. what!? Nana came into town for our birthday!

Bailey looked up to the ceiling of the car screaming internally. He started with a peace offering to get her past going to get eyelash extensions and lip filler without her so she could clear this up and it turned out she didn’t even know.

Candi: I knew you and Miss Gates were coming to pick me up, but I didn’t know for what. OMG OMG I am so excited!

Candi: I haven’t seen her in years! Are you on the way now!?

Bailey: We picked her up already, something about flight being early.

Candi: Yay!!!! Don’t you just love her! I bet she just loves you!

Bailey: yeah… she thought I was you

Candi: NO!

Bailey: YES! HELP!

Candi: that is almost perfect

Bailey’s green eyes bore into his phone, his friend wasn’t in front of him, but he could practically see the wheels turning in her head through the device.

Bailey: I tried to tell her I wasn’t you and she slapped me!

Candi: Oh yeah, you shouldn’t make Nana mad

Candi: If she is mad at me because of you I will be so upset

Candi: Fine I will call her, and tell her all about how she met my little sis

Candi: I do love how she thought you were me

Candi: You should have picked me up first and we could have planned it better!

Bailey: That was the plan but I didn’t drive

Candi: Daddy promised I could get my license tomorrow if I pass the test

Candi: OMG you need to make sure you can come too!

Doing the best he could to get her to stop texting and call the old woman before things got worse he just kept agreeing and telling her to call. They were much closer to the hotel than he would have liked before the issue got cleared up. When the elder Connors got off the phone she looked into the back seat and gave that smile, that same smile her son had inherited from her. “It seems I made a mistake, I am sorry for striking you my dear. I thought you were my Candace playing a mean prank on me like I hear kids do on their tick tock shows. Who would have thought she would make a friend that looks so much like her, I can see why she calls you her little sister. If there is anything I can do to make it up to you, do not be afraid to ask.” Bailey smiled sweetly back at her, the blow hadn’t really hurt before it was just shocking. “Just show Candi the same love you were going to show me and we will be even.” Edna's smile grew wider hearing that. “Such a sweet girl, little Candace said something similar about you. You just need to watch that tongue of yours in the future, but again I am sorry for striking you.” Nodding to her Bailey looked back at his phone seeing Candi say it is all taken care of and looked back to the old woman who didn’t look terribly pleased Bailey had looked at the phone while they were talking. “Apology accepted and I’m sorry for being rude.” There wasn’t a reason to apologize to her, but he thought back to how he imagined the situation growing out of control and though doing so could only help things.