Preparing for a date

“Now I am only going to do this once for you pumpkin, but as you know it takes a few times to make sure you are clean down there. “ Bailey did his best to not whimper at the feeling of the tubbing going into his ass as he bent over the side of the bathtub on his knees with his ass in the air. His panties were on the floor next to him, his borrowed red skirt was pushed up and his rear end was on full display. When he was marched to the bathroom and told to take off his panties he didn’t even hesitate to do what Aunt Megan told him, his panties and white tights were quickly removed but as he stood there watching her fill the rubber bladder with warm water, soap and a few drops of perfume he considered telling her he wasn’t going to do that. Not again, the last time was terrible. A good girl is always obedient. A good girl never argues or complains. His mind reminded him of his place and some of the consequences of being a bad girl.

So he said nothing as Aunt Megan started to fill his bowels with the soapy perfumed water. “I have a few things to take care of, but you redo this yourself until everything comes out nice and clean.” With that he was left alone, feeling himself getting more and more bloated. It was uncomfortable from the start and worked its way up to pain before he was able to sit down on the toilet and release everything that was held inside of him. He didn’t have to look in the bowl to know he wasn’t clean, the little bit of perfume in the soapy water did nothing to hide the smell of what came out of his bowels. So he had to refill the bladder and do it at least one more time. Aunt Megan used this as punishment before, and it felt worse that she had left him to do this himself and he was doing it without even the hint of a threat from her. Though he could imagine plenty, like if he refused she would do it anyways and instead of letting him vacate his bowels she would shove a tampon in his ass and send him outside to play with a jump rope.

He felt wiped when coming out of the bathroom, he hadn’t even bothered to put his panties back on knowing he had to get changed for his date and he was going over what he had in his suitcase that he could wear and how to style his makeup. “All clean pumpkin?”

Aunt Megan was walking out of her daughter’s room, the room he was staying in. She was wearing a silk robe that went to only halfway down her thighs, her hair was done up with a braid around the crown of her head, her bangs teased out with long strands to frame her face, while in the back she had added a mild curl to all of her hair that came down. She had smokey eyeshadow and had used her eyeliner to give herself a cats eye look. She wasn’t wearing lip gloss or lipstick so Bailey knew she wasn’t done getting ready, but she looked incredible. The robe hardly held in her large chest and he could feel his trapped member letting him know of its approval. “I am and you like look very pretty Aunt Megan.” Bailey hated that he was attracted to this woman.

“Aww that is sweet of you to say pumpkin. I would say it is time to start getting you ready, but I was going through your suitcase and I noticed you didn’t bring your applicator or your cream.” The raised eye let him know this was a question. “Ahh umm yeah, I like didn’t think I would need it.” Megan smirked and nodded her head before she turned and headed back into the room. The suitcase was open and on top was a three pronged vibrator toy in a new packaging. Bailey’s jaw fell open as his eyes went wide, it was the same thing Candi had, but this one was pink. “Didn’t think you would need it because you got yourself something new you wanted to try out?”

That thing was not there when he pulled out underwear to wear this morning, but then again he didn’t remember closing it up either and when he went to grab it this morning to put in the car it was sitting ready for him on the bed. “No, ahh umm I think Candi must have put that in there.” Watching Bailey this once macho in your face man who despite his small size would look everyone in the eye to try and stare them down, now look like an embarrassed teen girl shuffling her feet and trying to look everywhere but at her made Megan smile.

“Well that seems kind of her, but you shouldn’t leave what the doctor gave you behind like that missy. I recall the instructions saying you needed to use the cream with it once daily.” She lied knowing it said once every other day.

“I don’t need it… or want it.” Bailey into Aunt Megan’s blue eyes something in him told him to die on this hill. That he would not use a dildo to fuck himself, what was going to happen if he didn’t? At worst this thing would have to come off and that was a good… no, sugar a great thing! “Are you a doctor?”

“No, but…”

“Bailey with your grades and IQ you would be lucky to be accepted into nursing school. I’m sorry that was a bit harsh, but you have to understand that your doctor knows what he is talking about. We can pick up your cream tomorrow, but for now I think it best we at least use what your big sister got for you. Why don’t you go grab your phone so you can take a photo of it and tell her thank you.”

As he walked out of the bedroom, Megan stepped into the doorway to watch Bailey move down the hallway into the living room. She wasn’t sure at first, but Bailey was walking on the balls of her feet. “Isn’t that interesting.” She said to herself. So much for dying on that hill Bailey, you didn’t even fight back. He mentally grumbled to himself as he picked up his phone that sat next to the piece of paper he had been writing on.

Bailey Ann Best marries August Gates, Bailey Ann Best-Gates, Bailey Ann Gates

Our children - If we had a boy he would have like brown or blonde hair, maybe light brown when they mix? But totally have green eyes and he would be slim but strong and tall like his Daddy!

Names, umm Noah, Andrew, oh oh August he could totally have his Daddy's name and be a junior! No one wants to be a junior but like when he grows up he can name his son the same and he would be August the Third and that would be so cool!

A little girl!!!! I would put her little blonde hair in pigtails and she would also have green eyes like her Mommy, she would like totally be a mini me. It would be okay if she had her Daddy’s eyes though.

For names maybe I would use my middle name for her first Ann or like name her after my Mommy or Aunt using their middle names Lilly or Rose. Oh I really like Lilly, I could have a little girl name Lilly Gates!

Bailey Ann Best marries Liam Summers, Bailey Ann Best-Summers, bailey Ann Summers

Our children I’m like a blonde and Liam has brown hair, but it has like a hint of red in it and he has these big blue eyes. I could totally think of us having little ones that have blue eyes and my blonde hair. Oh could you like imagine if we had a little girl and she had blonde hair, but one blue eye and one green one!

For names I like still like Noah and Andrew and I’m really thinking about naming my first baby girl Lily Ann, it is just so pretty!

Looking down at the letter Bailey felt a little disgust, not how his handwriting looked so girly with hearts over letters or how it flowed. Not even the pure ditziness of how he wrote, all of that was normal to him after writing in his diary everyday, but at the thought of walking down the aisle in a white dress to those men, or any men let along spreading his legs to let them try and impregnate him. With how realistic this thing was on him he really hoped they didn’t have some upgraded model that would allow him to get pregnant or some sci fi thing like that.

On his phone were a few messages and he clicked through them, doing is best to delay what he knew was coming.

Auggy <3 : You looked beautiful in your church outfit, always appreciate you sending me pictures of you.

Auggy <3 : Just wanted you to know I was thinking of you.

Bailey: Aww, I was just like writing about u

Auggy <3 : Writing about me!? Anything good?

Bailey: What do u think of like rainbows and unicorns?

Auggy <3 : Sounds like something I might want to read

Bailey: Maybe if your good

Auggy <3 : I’m always good! Well, maybe that is for you to tell me ;)

Bailey: I will tell u about the story l8er :)

Liam: Excited to see you tonight

Bailey: Aww that is sweet

Liam: Yeah that too, but I’m EXCITED to see you tonight

Bailey: Oh oh, oh!

Liam: Can’t help it thinking about your hot body

Liam: If you are upset maybe you could hold it against me

Closing his eyes Bailey put his hand on the wall as he let out a long sigh. Glancing down at his feet he frowned for a moment lowering himself down off the balls of his feet. He had just douched himself clean, after writing a girly love letter about a figure marrying two different men, currently stood in the hallway flirting with those same men over text and was about to use a vibrator. How had his life come to this? “Bailey honey, are you coming?” He heard Aunt Megan’s voice and started moving once again. It was her doing, Aunt Megan had blackmailed him and **** him into all of this and he couldn’t even say it was one step at a time, it felt like he was pushed into the deep end, while slowly learning how deep it really was over time. “Coming Auntie!”

Looking into the mirror over the dresser Bailey shook his head as he looked at himself, but more lost in thought at what had just happened. He had shot off a text to Candi with a picture of the vibrator she had bought him, he had been with her almost all the day and wasn't sure exactly when she had to the time to slip that into his bag. He knew she got a package and said it was something for self care, but he hadn’t even seen her open it. When he opened the package Aunt Megan made him strip naked and lay on the bed, the way she looked at him reminded him of being in the doctor's office. “I want you to start off by picking a picture on your phone of one of the men you like. Maybe it is Derrick, Charles, August, Liam, that nice boy Jeremy or even that police officer that called you. What was it? A gun bunny or a badge bunny?”

“I like don’t have any pictures of him.” He was already blushing as she named off men in his life and thankfully she didn’t know about the lifeguard, but when he replied he knew he errored. “Aww that is too bad pumpkin, you will just have to choose on your own. What hunk in your life are you going to look at while you pleasure yourself?”

Just like with the douching she was making him do it and he thought it was worse, but he wasn’t sure if it really was. Some things she had chosen in the past were much worse and he didn’t want that, but at the same time he didn’t want to pick what image to look at while he used a vibrator on himself, he didn’t even want to do that part. Derrick, August, Chuck, Liam, Jeremy… Jeremy was still wasn’t eighteen and the idea of a boy let alone a minor was not going to happen. He already knew was August dick looked like and the last thing he wanted to do was picture it while he touched himself. Chuck was his oldest friend and he had seen his equipment in passing at the gym, the man was his oldest friend and Liam was his little brother, he had practically trained the kid so he could pick up tail. That left Derrick… he had seen him kissing Mommy so many times now. Bailey shook his head not wanting to follow that train of thought any longer, all the options were just so bad.

“No? You don’t want any of them? How about a celebrity you have a crush on? If you can’t decide I will play some porn for you. I know that will get you in the mood, maybe something with a shirtless fireman.”

He thought of his favorite movie P.S. I love you and how Holly was in love with Gerry. Gerry was Gerald Butler. It wasn’t really his favorite movie he reminded himself, but he had watched it at least ten times since this ordeal started, he felt like he could play the part of Holly at this point. Move over Hilary Swank, Bailey Ann Best is gunning for the part you already played. Bailey rolled his eyes before pulling up an image of Gerald Butler on his phone, the first image coming up was him from three hundred, shirtless. “Mr. Butler, good call Bailey, you have good taste in men.”

“Now pumpkin, remember, one hand on one of your breasts. Start to rub them around and across your nipple, it is okay to touch yourself and to find pleasure in it. Then move your other hand down and start to feel around, touch yourself, see what feels good, what you enjoy. Then and only then do you bring in your new toy.” He did as she said and wished his chest wasn’t so sensitive as the shock of pleasure ran through his body. Bailey knew it shouldn’t feel like this, this is what girls felt and he was a man. It was just some hormonal problem, yet just touching his chest was making him so turned on. His dick started to swell, it didn’t really have anywhere to go and every time this happened it felt uncomfortable, but that was only a small distraction from the pleasure.

Then when his hand went down to the fake pussy he had attached to himself he felt only the pressure from his finger as he inserted it into himself. As he felt inside he could tell the top of the tunnel pushed down as his trapped dick that was getting harder and harder tried to to move from pushed back to standing straight up, but if he didn’t know better it was like the vagina was doing its best to welcome and hold this finger. Being inside of himself added nothing to the experience for pleasure, but when his thumb moved up to the false clitoris the vibrator wrapped around the head of his dick came to life right away.

The thing glued to him was supposed to be for transgender people, but with thow sensative it was and how high the vibrator went it felt more like the thing was meant to just pleasure yourself. It felt so good, and Bailey closed his eyes to enjoy it when he felt a light smack on his calf, reminding him Aunt Megan was standing right there and he was supposed to be looking at the image on his phone. She let him, more like made him continue for another minute before she motioned to the pink three pronged vibrator. The thing would insert a little into his ass, the fake pussy and to his oh so sensitive clitoris.

Bailey shook his head again the idea that he was getting off on touching his chest and using that thing was baffling to him, but it had felt so good, like incredibly so. Part of his mind told him he shouldn’t even admit to such a thing, but if Aunt Megan hadn’t stopped him from continuing he would have cum. For a moment he was mad at her, but he dared not ignore her command. With a flushed face she helped him up from the bed and showed him what he was going to be wearing for the date tonight. A pair of thong lace panties a tiny leather black skirt, a white halter top with thin straps and lace just under his bust. It looked like something he might wear to bed, not as a blouse.

He now wore them along with the almost knee high black heeled leather boots. She gave him no bra to wear and to accessorize gold earrings, they were small hoops, but were thick. On his right wrist he had twin thin gold bracelets and one thick one on the other wrist. Bailey wished he could wear the green dress he wore on his last date, not that it was an option with the stain he still needed to ask Aunt Megan how to get out. In this outfit he felt like he was dressed like some slut. “You are looking lovely tonight Bailey, I’m sure that outfit will get your date's attention. You know I never let my daughter wear that, I think I might have told you that already, but I think it suits you. “

Looking away from the mirror Bailey looked at his Auntie, she was wearing a maroon dress, with three quarter sleeves, that showed off her impressive bust, the skirt was tight and long enough to be just a few inches above her knee. While he wasn’t sure if it was part of the dress or something she added, around his middle was a black wrap that secured in the front with a little bow. On her feet were a pair of black patent leather rounded toe heels with a thick ankle strap. After looking at so many shoes on pinterest with Candi he instinctively thought how cute they were. The woman was dressed to kill and after coming so close to getting off but being denied he felt it revving his engine. “Wow Aunt Megan you look gorgeous!”

“I appreciate you saying that, and I hope Charles feels the same. As you get older it becomes harder to keep a man looking at you like you are a present for him to unwrap.” Earlier she stopped Bailey, watching her eyes focus on the picture of the shirtless man, while touching herself and using the vibrator and her little moans had gotten herself worked up too and she couldn’t stay in the room any longer. She wanted to make sure her date was as excited about the after date time as much as she was. Her little sister was with the right man now, but for a little fling having a younger man in the bedroom, she had the right idea of that, she just let it go on too long. She couldn’t wait to tell Amanda about the letter she found Bailey writing after church today, it would be another nail in a long line of nails she had been working on to seal the coffin of her ex boyfriend.

“Honey, the men should be here before we know it, but why don’t you go sit at the kitchen table with your laptop and play your game for a little bit while you wait.”

Bailey truly didn’t want to play that game, but he would sit there and play it all through the night if it meant he didn’t have to go on a date with Liam, not that would ever be allowed. “Umm Auntie, I have been meaning to ask this and umm.” Bailey already felt his cheeks blushing, he could have looked it up online but the dress was dry clean only so he was afraid he would end up having to ask her to take him anyways. “On my date with August, I got something on my dress and I wanted to know if you knew how we could like get it off, but also like the dress might say dry clean only and if that is..”

Megan held up her hand to stop Bailey’s rambling. “You got something on your dress, but it is dry clean only. I imagine you can take it to the dry cleaner and they will take care of it. Wasn’t your mom still in town after your date? Why didn’t you just ask her?”

She watched as Bailey’s almost constant smile faltered a little, though didn’t vanish as she acted sheepish looking at the ground. “Umm well I didn’t want her to see what I got on it and with everything.”

“Sit it out girl, I can’t help if you don’t tell me everything.”

“I got cum on the dress.” Bailey said in a small voice.

“You got August’s cum on your dress?”

“Peaches I umm no, umm yes I mean some might be his.”

“Bailey Ann, look me in the eye this instant and tell me what happened.” He slowly slid his eyes up to her, his face felt like it was on fire with how embarrassed he was. Just talking about it made him remember the incident. He really didn’t want to, but ended up telling Aunt Megan about everything that happened.

“You shouldn’t be embarrassed, I experimented with a girl in college myself. That doesn’t make you a lesbien, especially when you clearly like men so much. I know you got caught giving a boy a blow job on the way home from school last year, but it sounds like I was right to make sure you cleaned yourself out for tonight.”

“Aunt Megan I like don’t want to have sex with Liam!” He put his hand over his mouth, he hadn’t meant to raise his voice and was afraid at what she might do for that or for saying he wasn’t going to have sex. He was sure she wasn’t going to be happy till it happened.

“Aww.” Megan wrapped her arms around Bailey. The idea of the piece of trash having to suck a few dicks after how often he cheated on Amanda was a delight and hearing it from Bailey’s own lips, that was the best thing she had heard all day. It beat the letter about marrying and children by so much, yet she never really expected things to truly go so far. The douching was because she knew he would hate it and to see how far she could push him to do things on his own, but he was considering actually having sex. That was a dream, she wasn’t sure how well the prosthetic would really work for that, though it looked real enough in practice. “Bailey honey, listen to me well. You never have to have sex with a boy because he takes you on a date or does something for you. If you don’t want to have sex simply do what you love and give him a blow job.”

“I…I don’t like have to have sex with Liam?!” The hug and the little pep talk about not having to have sex came at a complete surprise to Bailey, he thought she was making him do it. She never threatened him with have sex with Liam or you will get punished, but with everything it just felt like that was where she was going. That meant that was all his thinking, he had thought about having sex with Liam on his own. Peaches, peaches, PEACHES! What was wrong with him? With the new information and beating himself up it took a few seconds for him to realize what she had said at the end.

“Of course not pumpkin, you can wait to have sex when you are ready. I’m not silly enough to tell an eighteen year old girl she can’t have sex, I’m just advising you to make sure you really want it first.”

“But.. like I do have to give him a blow job?” If she was not pushing him to have sex he wanted to know, no needed to know if she was actually going to make him give a blow job. With what happened with August he had little choice with Miss April’s threat, but he wasn’t sure if Aunt Megan had ever said the same. “Bailey, of course not. I would never tell my niece she had to put a man’s cock in her mouth, that would be crossing a line. Tomorrow we can go pick up your cream, dildo and your dress and drop it off at the dry cleaner. If are too embarrassed I will even talk to them for you.”

Bailey let out a breath he didn’t know he was holding as relief ran through his mind and body. “It isn’t like you are my little sisters ex boyfriend who cheated on her constantly. If you were him I would say you had to suck on Liam’s dick, while moaning like it was the best thing you have ever tasted. If he didn’t do what I said who knows what I would do, he definitely wouldn’t be a good girl. So tell me pumpkin, what do you plan to do tonight?”

She was evil, like the mythology about punishment in hell was nothing compared to her. Sure she wasn’t going to **** him to have sex, but she set him up perfectly to believe she wasn’t going to make him do anything with a dick and then turned it around so he ad to admit he wanted to do it or else. Or else could mean taking her niece to one of the brothels to try out a few men or invite someone over. “Well like I was thinking about making sure Liam knew I liked him and I did tease him with the picture of handcuffs and the gag.”

“Don’t worry pumpkin, I won't tell your mom, just make sure you swallow tonight so we can have one less thing to drop off at the dry cleaners.”