Sucking punishment

Bailey looked down at the dildo in his hand, he hated the sight of his own pretty glossy nails holding the thing. He looked up to Megan and swallowed hard before opening his mouth and sticking out tongue, cringing as he moved the rubber phallus to his mouth. Just as he put the tip in his mouth Megan let out a laugh full of amusement. “I can tell you are in a rush, but I think we are forgetting a few steps.” she said pulling out Bailey’s phone and with a few taps of her fingers had it unlocked. The shock that Megan knew the unlock code on the phone that he had set just the other night after she made changes when it didn’t have a code was palpable, almost as palpable as the fake cock in his mouth. Slowly pulling the thing from his mouth Bailey’s eyes widened as his brain ran a mile a second trying to think what she was doing with the phone and what she could see and do with it.

The older woman placed the phone at the foot of the bed so that it was propped up so Bailey could see the screen. In front of Bailey was the image of Chuck, his best friend holding up a pint of beer like he was saying cheers and looking happy. “I took this the other night, me and that young buck had a good time. He really is broken up with how his friend left town without saying a word. Don’t worry I was there to console him, I mean how could he really have been a good friend if he just left town without saying a word. Now you can go back to what you were doing, and don’t forget to put your hand in your panties. I wouldn’t want to deny you your release, and make sure you stay in character. Unless you want to do one of the other tasks I laid out for you. Bailey’s face was a grimace as he looked at the picture on the screen, realizing Megan must have just sent him that photo. A single tear ran down Bailey's cheek before he wiped it away and he felt like many more wanted to join it. Trying to push through it Bailey looked to Megan and then the photo and finally to the object in his hand. “Okay…” he said in a soft voice. “He is really cute.” he continued before giggling.

The camera on Bailey’s was taking video capturing the images of the teen girl from just below her breasts up as she looked forward to it and brought the dildo to her lips. She gave it a little lick and gave a coy smile. “I wonder if he is bigger than this.” she said before wrapping her glossy red lips around the flesh colored dildo. Her cheeks pulled in as she suckled and worked the object in her mouth going a little deeper after each time she pulled back. “Mmmm, MMMM!” she purred before pulling the dildo out. “Chuck I wish you were here, I wish this was real.” the words sounded line a whine or as if she was begging the universe to grant her desire. The camera couldn’t see what was happening below her waist, but it could see her arm moving as if she was doing something with it just out of sight. The camera wasn’t seeing how Bailey had his panties pulled down just enough for his erect member to be rubbed on. It took a bit of work to get it hard as nothing he was doing beyond touching himself was exciting to him. Bailey had no idea the camera was rolling, only that Megan was sitting at Mandy’s vanity facing him and rubbing her own legs together. Bailey wasn’t sure, but a guess would be she was getting horny seeing his cock.

Fuck, if she wanted my dick we could have worked something out. He almost thought how he wouldn’t cheat on Mandy with Megan, but more than once he had a dream about being in bed with the two of them. While he suckled on the fake dick Bailey closed his eyes and pretended the fake dick was his own and he was part of that very fantasy. His eyes opened just enough to see though his long mascara covered lashes to see Megan, letting the image of her getting horny fuel his imagination as if she was there for him. Bailey started to rub his nyloned legs together as his hand jerked, twisted and squeezed his dick while his mouth worked another. “Mmmm, yeah, yeah, oh that's good.” he moaned breathily before returning the object back to his mouth. Bailey was trying to get lost in the fantasy, the further he got from the truth of what was going on the less and less he felt like curling up in a ball and crying. As his own hand started to get covered in precum Megan motioned for him to swap hands. Giving it no real thought he did and regretted it right away. His tongue let him know he was tasting a now slightly familiar flavor to what he experienced at the movie theater. Megan turned her head to the side and mimed Bailey deep throwing the phallic, so he did. Bailey’s green eyes went wide pushing it back, right away he started to gag. The sound obvious, but still Megan held the pose and held for way more uncomfortable seconds than Bailey would have liked before pulling back. Pulling the now slimy object from his mouth, the feminized man took a few deep breaths, even stopping his own pleasure before returning to the task as his task master motioned for him to continue. With her stopping her instruction Bailey was just starting to fade back into his imagination, imagining it was Megan who was gagging on his cock. As the white sticky substance shot down and pooled on the bed spread where he was pointing his cock Bailey pulled the dildo from his mouth out of breath and happy with the lingering image from his imagination of cumming all over Megan’s face.

Leaning back on the bed Bailey let out a deep breath as Megan came up to the foot of the bed and picked up the phone. Now feeling spent, Bailey closed his eyes, hoping now the witch would go. “That was a lovely show.” Bailey could feel the bed shift as Megan sat on the bed next to him before he felt her weight leaning into him. “Would you like to watch it with me?” Bailey’s eyes snapped open as he saw Megan holding her own phone that was playing a video of Bailey going to town on a dildo, all from the perspective from the foot of the bed. “What?! How?... oh no. No, no no.” Megan leaned over and gave Bailey a kiss on the forehead. “Oh yes, now I know I didn’t need this extra material to **** you with, considering how I have you with a hooker in your girlfriend's bed, you in a changing room with a minor, but you know me. I just love leverage.” Megan got off the bed and made a face seeing the small pool of cum on the bed. “I think you will need to add your mom’s things to the laundry today. Now come on, let's find you a nice outfit to wear before we get to your hair.

Bailey didn’t have much of a choice when Megan handed him what he would be wearing. Soon he was wearing a white petticoat, a sleeveless red with white polka dot dress, a white belt and some pears for a bracelet and necklace. The last two were things he had bought Mandy once upon a time. “Amanda thought it would be fun to have this retro dress, but seeing it on you I can tell it would have been too short on her. Though maybe that was the point, for you though, Bailey you look lovely.” Not so much as giving the woman the satisfaction of a groan, he just smiled at her and glanced at the mirror. The petticoat made the dress poof out and the overall image made him look like a fifties housewife who just got fucked, considering both the woman in the mirror’s make and hair were a mess. Megan took Bailey by the elbow and brought him back to his room, dropping him off on the vanity seat and putting his phone down in front of him. On the screen she had a queued up video of how to put his hair up in hot rollers. “Watch this, and I will be right back.” the second she was gone Bailey went into his phone to delete the video, but it was already gone. There was no link to it or download icon to ‘Aunt Megan’ in the phone or any cached email addresses in the browser for her to send it to herself. Bailey started to make a fist and squeeze before he stopped from the sudden pain of his dainty nails reminding him of their presence. Tilting his head back Bailey opened his mouth wide to let out a soundless scream that shook his body before he ran out of air. The tears that he held back before now came back with a vengeance and Bailey could feel they had no intention of being stopped this time. Quickly he stood up and hopped over to his girly bed and wrapped his arm around the token of his love for Mandy, the teddy bear and wept into one of his pillows.

That is how Megan found the disguised man when she returned to the room. She pressed her lips together before putting the hot roller kit down on the vanity and plugged them in to prep them. The sight of the pretty blonde girl crying her hair out as she clutched her stuffed animal made Megan feel bad. She didn’t think of herself as a monster, she saw Bailey as the beast and her the tamer. The beast would either learn its place or flee, but looking the part of a **** girl moved her even knowing who it was. Sitting on the edge of the bed Megan rubbed her hand on Bailey’s back gently and shushing him. When he turned his head to look at her from the pillow the expression was of agony not of anger. With a little pull Bailey came into Megan’s arms, now sitting up the two hugged. Bailey still balled his eyes out, now into Megan’s shirt and wished he had more control of himself to push her away. Right now the embrace felt good and the release of emotion was all that mattered. When the tears subsided Megan pulled back and wiped her finger over one of Bailey’s cheeks. “Feel a little better?” with a sniffle Bailey nodded his head. “I know I’m hard on you, but I tell you what. I will promise to do my best to treat you like the niece I love if you can act like her. That means no more punishments so long as you keep your end of the deal. Okay?”

No thoughts of lashing out or throwing blame came to Bailey, he felt so drained after cumming and then crying his eyes out for what must have been twenty minutes and a good part of that in the arms of this woman. The idea of being treated well was more than appealing and fighting back really hadn’t won him any ground so he nodded to her. “I, I um promise to be a good girl.” the words, that promise felt like they physically wounded his pride. “Good, now why don’t you sit back down and clean up your makeup while you watch that video. You know you are getting very good at that, I really am impressed.” Megan said as she stood up and gave Bailey a kiss on the top of his head. “If you need help come get me, I have to take care of something.” she said as she left the room and headed to the bathroom.

Once inside she locked the door and pulled up the video of what she just made Bailey do with the dildo. She felt bad for all the crying, but having that kind of control over him and seeing him give a pretend blow job to a man she just had eat her out the other night was intoxicating. While Megan took care of some of her needs Bailey did as he was instructed, fixing his makeup and trying to learn how a girl puts her hair up in large hot rollers. When the video was over Bailey hit reply so he could finish up his makeup before getting started. The task was harder than he thought it had any right to be and did end up requesting Megan’s help when she came back. Despite trying to set course for smooth sailing with their relationship Bailey shouldn’t couldn’t help himself from being nasty when Megan ran a brush through a tangle. “Not so hard you harpy!” he said and as the words left his mouth Bailey was sure he was about to feel another slap like he felt earlier. “Auntie, I’m sorry.. I, umm, I’m so sorry. I shouldn’t have said that!” Megan who was standing behind Bailey looked at the thick hair brush that she knew Amanda used to brush her new daughter's hair to make it shine and smiled. She considered using it to turn Bailey’s rear as red as the dress, but a glance at the vanity gave her a better idea. “I know that must have hurt, I’m sorry too. I should have tried to be more careful or warn you that it might hurt. I tell you what, you watch and learn how to do this and then you can read to me a few chapters from your diary I got you. I would just love to hear about your inner thoughts and dreams.” Bailey looked at Megan in the eye through the mirror and gulped. “Like fur sure, I would love to!”

It wasn’t long before Bailey was sitting at the vanity facing away from the mirror, legs crossed at the thigh and facing Megan who was seated on the teen’s bed. Opening the pink book Bailey started to read the first two entries out loud, just as if just reading them, but trying to give everything as much emphasis as he thought Megan would want. The last thing he wanted was to have to start over again to do it the way she wanted or worse, go back to one of the other punishments she mentioned earlier. At this point if Megan took him to the brothel to pay a man to have his way with Bailey, he wouldn’t be returning till after Mandy got home, not with having to wait for the rollers to do their job. Then she would ask about where they went, he couldn’t imagine paying a man to fuck him and then having to tell his girlfriend. So Bailey did his best girly girl Bailey act and read to her favorite Aunty.

Authors note: another author CDbaby did the diary entries for me, if you have not clicked on those paths then give them a read to have an idea of what Bailey told her Aunt.
https://chyoa.com/chapter/Popcorn-and-a-happy-ending.919996
https://chyoa.com/chapter/Bailey%27s-like-totally-awesome-day%21.918357
https://chyoa.com/chapter/How-I-became-a-mom-and-a-little-sister-all-in-the-same-day.918662