Saturday night before bed

Amanda kissed her boyfriend on the cheek, letting go of him. “I promise to help you stay in character my love. Could we maybe save that for tomorrow though? I want to show you just have appreciative I am tonight.” she said with a hungry smile. “All of this will have to go though, as you know I do not do the lesbian thing.“ she said waving her hand around Bailey indicating his entire teen girl look.

“We can just pretend Bailey your teen daughter went to bed in the other room, while you invited your boyfriend to the bedroom.” with a wide smile on his face Bailey took off to the master bedroom, unaware of how seductive his walk was in the wedges from Megan’s lessons. Auntie it seemed wanted to make sure her niece had a walk to draw the eye of every male that could see her.

While Bailey went off to de-girlify himself Amanda took a few more sips of the wine before dumping the rest out in the sink and cleaning the glasses and wiping down the table.

Walking into the room and pulling the pink lace shirt over his head Bailey tossed it to the floor and sat at the edge of the bed to untie the bow for the heeled wedges that the Connors were so kind to give as a gift. After them were the long socks that got bunched up and tossed to where the girly blouse lay. “At least today will end on a high note.” he said popping back to his feet and unclasping and unzipping the baby blue skirt, adding it to the pile. Standing in the room in nothing but the pink lace bra and panties he reached behind his back and after some fussing was able to free himself form the contraption. Feeling the weight now unsupported by the bra he looked down and remembered he couldn’t remove the breasts. “Oh yeah, that...” he said with some defeat in his voice and with a sigh removed the last vestiges of the female clothes.

Going over to the dresser Mandy and him share he pulled out some boxers and slipped them on, but in the large mirror over the dresser he was reminded of the hair and makeup. “That will have to be next.” he said pulling out a T-shirt and slipping it on for bed, but it just didn’t fit with the C cup breast now attached to his chest. The shirt bulged out front and made it uncomfortable to move in, so he removed it stuffing it back in the drawer. Thinking for a second, he reached into Mandy’s drawer to pull out one of her shirts. Looking in the mirror at the large globes on his chest, if they weren’t on him, he would love them, he thought as he reached up and rubbed both of them. The image in the mirror was turning him on so he had to stop. Covering the breasts with Mandy’s shirt seemed like the best option, no way would she be down to seeing another set of breasts as they made love.

Bailey was walking into the bathroom just as Amanda walked into the bedroom and spotted the pile of clothes. Picking them up she walked into the bathroom to put it all in the hamper and tell Bailey for at least the tenth time this week to not put clothes on the floor when she stopped seeing her boyfriend wearing her peach-colored nightshirt that said Victoria Secret across the chest in pink, while he had some wipes in his hand leaning closer to the mirror to remove the makeup. With his hair still braided it looked just like a girl getting ready for bed. “Bailey honey, it is normal for a daughter to borrow her mom’s clothes, but I thought we were not doing any of that tonight.”

Looking at his girlfriend in the mirror Bailey had a sheepish look on his face. “The stupid tits make my shirts not fit.” the comment made Amanda laugh out loud a hearty laugh.

The thoughts of reminding him again about the clothes on the floor left her from the fully on belly holding laughter. The odd day and situation were just too much, and it all came out in laughter. At first Bailey looked annoyed to be laughed at, but it was the type of laugh that was contagious when you cared for the person doing it, so soon he was joining her in the cathartic exercise. When it all died down, she left out a long happy breath and put the clothes into the hamper and smiled before starting to remove her own clothes, stripping down to nothing while Bailey watched. It started as her just taking off her dress, but when she noticed her boyfriend watching, she slowed her pace down, teasing him with the show.

With a wink Amanda walked out of the bathroom turning off the light switch knowing Bailey would be following and watching. Crawling onto the bed naked as the day she was born Amanda swung her ass from left to right looking over her shoulder giving a small smile and another wink seeing him standing at the end. Bailey reached out to cup and caress her rear, but before he could touch, she pulled herself deeper onto the bed, turning around on her knees before sitting on the still pristinely made bed from the morning. Bringing both hands to her hips she slowly raised them, gliding them across her trim figure before coming up and cupping her breasts. “Mmmm.” she moaned while biting her lower lip and closing her eyes, enjoying the feeling of her own hands across her erect nipples.

Climbing onto the bed Bailey brought his left arm across Mandy’s lower back, sliding it up and down, each time coming closer to rubbing his fingers over her ass. While his right reached up and caressed her firm breast, at the same time he leaned forward pressing his mouth to her’s. The two touched each other softly, kissed softly. Pulling away from her mouth Bailey kissed down the slender neck and onto the collar bone, while Amanda vocalized her pleasure feeling him trailing down to take her other breast in his mouth. “Mmmm yes.” she purred feeling the pleasure of the mouth over her nipple then the cold air of the room when he came back up to kiss her deeply pushing his tongue into her mouth.

The kissing moved from slow and tender to more passionate. Fiercer.

Amanda pulled Bailey closer to feel his body to press into hers, both still kneeling on the top of the bed. The feeling of the smaller breasts on hers bothered her and she pulled her face back and loosening her grip on him. Her blue eyes looked deeply into his green trying to work through the odd feeling she just felt, but her eyes closed once more as Bailey leaned forward pressing her back down onto the bed and her side pressing his lips to hers once more and to explore her mouth. Their tongues danced, while Bailey’s’ hands roamed her body and one of hers reached under the long shirt and into the boxers feeling the firm member. Delicately she held it in her grip hand around the shaft and the pad of her thumb rubbing the base of the tip. It was Bailey’s turn to let out sound of pleasure as she did that and pulled it free of the cotton undergarment.

Amanda moved her hand on top of the dick twisting it lightly like she was screwing and unscrewing a lid down, before moving he fingers down the shaft to run her finger nails across it and to his balls. While Bailey shifted one leg between Mandy’s getting her to open her legs so his hand could have easier access. Pressing his fingers to her pussy and gently and slowly rubbing her clitoris he could feel her body shiver in pleasure. Bailey desperately wanted to fuck Mandy, but he always made sure to get her off with his hand or mouth before they ever went further. The last thing he ever wanted was to leave a woman without getting off if he ever came before she did. Circling the clit and varying his tempo Bailey only gave light pressure, and slowly increased it. Listening to her breathing, she was getting faster indicating he was doing it correctly. Sliding two of his fingers inside her Bailey could feel how wet she was and slowly pressed in deeper with the index and middle finger while his thumb rubbed up and then around the clit before starting the pattern again. Getting the dexterity down for the two things at once took time to learn and had been an eager student. While his hand worked, his mouth went back down her breasts.

Bailey’s mind wondered in the pleasure of her hand rubbing on his cock while pleasing her, it was a balancing act with how pent up he had been. It might have been because of the three glasses of wine, the exhaustion, or how hard he tried to stay in character all day. But when he was fingering Mandy, her breathing coming rapidly he moved his mouth up to kiss her neck and whispered “You like that don’t you mommy.” trying to sound seductive.

Opening her eyes wide Amanda looked at Bailey saying “What!? No, god no. Get off!” seeing now with the lights still on in the room with them a top the bed Bailey’s hand, some fingers inside of her, but the glossy pink nails still present. Pushed him off her, his hand slipping free from inside her.

“What’s wrong Mandy?” Bailey said in confusion now laying on his back closer to the edge of the bed.

“That was just too much, the breast you have, the pink nails and hell Bailey your hair is still in a braid. We just cannot. Not like this. When this is all over, we will. get those off, clean off your nails and you are getting a haircut. Right now, all I am seeing is...is a girl. I am sorry.” the voice was a bit manic as she tried to get a hold of her emotions and calm her libido.

Bailey could still feel her wetness on his painted fingers, and with his cock still rigid as ever he nodded.

“I'll, umm, just go take care of this then, I understand Mandy.”

Leaving the room and closing the door behind him Bailey grabbed his laptop and went to lay down in the guest room. HIs member going down on its own, but he felt more pent up now than ever before. The horrid situations, that bitch Megan. This was all her fault, if it wasn’t for her, he could have gotten a blow job from that red headed whore Candy and then one from Mandy later that night and now.. He didn’t have either of those or sex tonight. “That bitch.” he said softly to himself.

Opening the laptop, he opened one of his favorite porn sites and figured he would watch one he had favorited and watched a few times. It was one of the tropes of the hot milf stepmom getting stuck and asking her stepson for help, only to end up being fucked. The video played, the male actor on the screen was running his hands over the woman’s ass. She complained but was going to get it anyways. With the entertainment going he started he lifted the peach long shirt and pulled out his cock once more as it started to wake up from the familiar video. Running his hand up and down and over his member he knew he wouldn’t last long. He closed his eyes enjoying the feeling and listening to the audio knowing already what was on the screen he tilted his head back to the ceiling trying to contain himself from crying out from the feeling. When he slowly opened his eyes and looked down he caught sight of himself in the mirror. The blonde braid coming over his left shoulder of his peach Victoria secret t-shirt, breasts visible while rubbing on himself, he licked his lips. Moving his other hand under the long shirt and working it up to expose the life like breasts he rubbing and tweaked the nipples. He couldn’t feel it other than some extra pressure, but the sight was intoxicating. With that and the audio playing he quickly climaxed shooting his load up into the air. Some of it landing on the shirt on the word secret.

Finally spent, after days of blue balls he felt content and pushed his laptop to the side and closed the lip and leaned back on the bed. Meaning to only bask in the afterglow for a moment before returning to bed with Mandy, but before he knew it sleep overtook the exhausted man and didn’t let go until morning.