A plan for work

Music blared from the cell phone with the flower case that sat on the nightstand next to Bailey bed. The energetic song from Wham picking up thirty or so seconds into the song. “Wake me up! Before you go-go, Don’t leave me hanging on like a yo-yo, Wake me up bef…” Growing Bailey reached over to silence the morning alarm. With the music silenced and his groan complete he stretched his feet under the covers before letting out a long sigh. “Monday…” He said the word like a curse to himself as he got out of bed. Sitting up on the edge of the bed he let his feet hang out down as he continued to stretch, his breast rising and falling with his movements as the cool air conditioned air reminded him of just how little protection his slinky little nightie provided.

Blinking a few times he considered getting to his feet before plopping backwards on the bed. “Gaaa!” Bailey whined, he wasn’t ever a fan of early mornings, but it hit particularly hard today. The weekend had been amazing, the love of his life had come home and they had talked things out. Then he got to see his old pony Cherry once again and got to spend the day riding. The day had turned into something magical, the ranch hand Ed had been a bit off and it had made him uncomfortable how often he caught the older man looking at him, but it did little to diminish the day. Candi hadn’t ever really gotten past the idea of sitting so high up and he was proud of her for hanging in there, though her complaining about how much it hurt riding a horse had him in more than one giggling fit, telling her how she should have stretched first like he said. This morning though, he was really feeling it, his lower stomach, inner thighs and groin were complaining. A complaint that was at least familiar to him, or at least once was, unlike what he felt when he had gotten Cherry up to speed. That motion had caused the vibrator attached to him to come to life in a practically spiritual experience. His emotions were already high and cumming in his panties hadn’t been something he had planned for.

“Wake me up! Before you go-go, Don’t leave me hanging on like…” Bailey sat up from the bed silencing his second alarm. Grudgingly he got to his feet with a slight pout to his plump lips, knowing he had to get moving, today he would be going to work with Mommy for the first time. Knowing he would see his chipper friend till they met up for work he sent her a few quick text messages, the pout shiting to a self satisfied smirk, knowing she would feel worse than him.

Bailey: MORNIN! How ya like feelin?

Candi: Hey, hey!

Candi: I don’t think I can walk

Bailey: Like tht bad?

Candi: Send an ambulance or like a hot yoga instructor

Bailey: I think I can like afford 2 send a whambulance!

Candi: With the hot yoga instructor?

Bailey: No you can try calling Ry

Candi: Mmmm he could help

Candi: That sounds like sooo much of a better day.

Candi: Ry using his hands 2 make me feel better and like Auggie for u

Going to work wasn’t something Bailey wanted to do, staying home and playing video games like he used to sounded great, specially when his body was sore, but Candi talking about the boys using their hands made his face grow flush as the recent memory of Auggies hands pressing into his flesh, touching and caressing his chest before his wet warm mouth sucked on his breast… Suddenly feeling like his bedroom wasn’t cool enough Bailey sucked in and let out a breath before answering his horny friend back.

Bailey:TBH I wanna sleep we totally have 2 go 2 wrk

Candi: FINE!

Candi: U always want 2 sleep

Bailey: No I dont

Candi: Yaaaa doooo, now like dont argue with your older sis

Bailey: Totally dislike u

Candi: Yaaaa doooont! U LOVE ME!

Candi: Now tell me what u r going 2 wear today

Considering the question Bailey sent his blonde friend a few more texts and a few pictures before scampering off on sore legs to shower and get ready for the day, a process that took much longer than it once did. Doing his best to not linger in the warm comforting embrace of the hot water and steam Bailey went through his moisturizing routine, using the face roller to boost circulation all before dashing back to his bedroom with his normal smile plastered on his face, knowing how much longer it would take if he had to share a mirror with Candi. Instead in his bedroom he was able to slip a headband on to keep his blonde locks from his face as he went about adding color to his dull features. With a last pop of color, some red to his lips he pressed them together making a kissy face in the mirror, almost reaching for his phone to snap a quick photo, before throwing that idea out the window.

Standing over his partially made bed, Bailey only wore a pair of cheeky black panties with a lace trim and a black with white lace trim balcony half cover bra that pushed Bailey’s feminine assets up in what he hoped would be perfect for his plan. On the bed was a light gray pencil skirt that he knew would end inches above his knees and a black blouse that only had the slightest hint of a collar, but was designed to have a plunging neckline. He planned to pair it with stockings so that the tops would show if he sat or moved in just the wrong, or in this case right way, and his pair of white five and half white rounded toe heels with hidden inch platform. Bailey’s left hand moved up so that his index finger could just lightly touch the corner of his mouth as he smirked. “That like, lecherous jerk won't know what hit em!” The feminized man was well aware how he would react to a hot girl dressing like this and acting all lovey dovey, and it was going to be perfect to get him to admit everything while his phone was set to record. With a happy little wiggle Bailey reached for his outfit for the day.

—-

“Good morning sweetie, I was just about to come get you.” Amanda said from where she sat at the kitchen table putting on her shoes before turning her head to see her feminized ex boyfriend. She saw Bailey with her hair up in a messy ponytail, minimal jewelry and an outfit that she would only wear on a day she was feeling particularly confident. A small smile on her face grew to touch her eyes, it wasn’t something she would ever really wear to the office, though she has seen a fair amount of young women dress like that to impress. What brought her joy was the fact that Bailey felt like she could dress like this, it showed just how much the person she thought she had known for years had changed, or at least changed enough for their appearance to match how they felt.

Returning the bright smile Bailey moved to give the woman he loved a hug. “Good morning to you too!” He wasn’t sure how he ever took her smile for granted, she wasn’t the bubbly ball of sunshine like Candi, she was a rock. Strong, unmoving and able to support those close to her and after having to put up with jerks at the office he now had a better understanding of what she had to put up with for years. He was not going to let Brannon get in the way of everything she had worked for. Today his girlfriend, the head of the accounting department was dressed much differently than him, while he dressed himself in a way to catch men’s attention, one in particular, she wore a well fitted women's suit. It was tailored to fit in a way he liked to see, but he also couldn’t ever remember seeing her wear something like it before.He blinked his long lashes at her for a second as she stood up to put on the outfit’s blazer. She wore a pair of well fitted black trousers that had a button holding the tight pants closed just above the ankle, a pair of pointed toe glossy black three inch heels, a white short sleeved blouse that showed a little less than his own plunging neckline, a tight gray woman’s vest and now a three quarter sleeve black jacket. The idea that he had sent what he was going to wear to Candi so she could coordinate as they often did and then to end up matching Amanda brought a slight giggle to his lips.

“What is so funny?” Amanda asked with a raised eyebrow.

With a slight shrug of his shoulders Bailey looked the beautiful golden haired woman over again. “I just like, don’t remember that outfit before.”

“And that is funny?” Amanda asked not really sure where the girlish giggle came from.

“Like, Well…” Bailey had his head slightly cocked to the side as he started to speak, not really sure where he was going with the explanation or why it was really funny, but stopped when Amanda held a finger up.

“I wanted to treat myself with the changes coming up, never had a real tailored suit before and me going shopping by myself is what you think is funny? Or were you going to ask to get a new outfit too because I did?”

Opening his mouth slightly Bailey was about to respond on reflex with a gleeful yes. Shopping had been fine, it could be down right fun with Candi around, but he really didn’t need any more feminine clothes. What he did need was to start a wardrobe for when the breasts he had on display today went away and he could start looking like himself. “Well… I could like totally use a few things.”

“I figured as much.” Amanda said with her happy smile as she reached out and caressed Bailey’s cheek. She wouldn’t be able to afford any type of clothing shopping trip this paycheck and really shouldn’t have splurged on the suit she was wearing now, but it had just felt so good to treat herself, explaining away the cost that soon she would be making enough money to afford such things. Buying things on credit that she didn’t have the money for, other than emergencies, wasn't something she did and hearing Bailey ask for more clothes made her feel a bit guilty. Bailey had gotten a large influx of clothing, but she was just starting out being able to buy pretty things and wear them. It made sense to her that Bailey back when she was her boyfriend bought her jewelry, dresses or shoes that were upscale, they were all things she wanted to wear. “Maybe next paycheck we can get you a few things. Never thought I would have to be trying to keep up with a shopaholic daughter.” She said with a laugh.

“I’m like, not a shopaholic.” Bailey said, rolling his eyes without thinking about it. The resting smile on his face giving the impression he was being playful.

“Mmm, well I for one am enjoying having a daughter I can go shopping with and spoil.” Amanda said, looking into Bailey’s green eyes.

Remembering how badly she wanted a family, to get married, to have children. How she was even willing to put marriage to the side with them committed to one another to have a baby… things he had all denied her. A spike of guilt ran through Bailey, he hadn’t been ready to marry and he really couldn’t give a true answer why. He absolutely didn’t want children, having to watch the little kid at the pool a few weeks ago while the kids parents probably went off to fuck had reinforced that, well that and the video game Aunt Megan had given him, the babies just never stopped crying for one reason or another. Here he was, pretending to be the child he never gave her, had a vasectomy to make sure of it, it all hit home hard on him after what he had gone through when she wasn’t around. “Umm, well, I guess since like, my ID says I’m your daughter I can let you spoil me if it makes you happy.”

“I love you Bailey, I hope you both know that and feel it.” The entire situation was more than odd, the man she used to sleep with wasn’t just transgendered and wanting to be female, but also continued on as if they were her daughter. She knew many people wished they could go back into the past and change things in their life with what they knew now, but all because of a mixup at her work Bailey was actually getting that chance. She had stayed awake feeling torn up about what Bailey was going through because of her, but knowing that Bailey was happy as her Bailey Ann, it made her heart swell with joy.

“I totally love you more Mommy!” Bailey said like it was a competition, a bit of Candi rubbing off on him with all their hours together.