Staying in the Family 15 (Patreon)

Later, after Shaun finished painting Nat’s toes, having to start again since much of it was ruined in the attack, he sat in silence as he drank his beer and watched the movie and let her nails dry. Even after her promise to be good she would still occasionally tease his cock with her foot. “Seriously–” he whispered, clamping his hand around her ankle–“why do you keep doing that?” he finally asked.

“My feet are killing me.” Nate whispered and pulled his foot free. With a heavy sigh Shaun pulled Nate’s foot back to his chest, “No!” Nate hissed.

“I’m not gonna tickle you.” He said gently, “Unless you misbehave.” He added with a smirk.

“You’re the one who needs to behave.” He argued, remembering how his last foot massage ended in the bedroom with his mouth full of–Nate glanced at Emma who appeared to be engrossed in the movie. Shaun wouldn’t try anything now that he knew the truth but…why was he offering? ‘Emma hadn’t told him to. So why?’ he wondered, unaware of the conversation that took place in Shaun’s bedroom. She would no doubt force him in heels again so this may be the only bit of relief he could get for god only knows how long and the foot rub up until the makeout session did feel good. Relenting he relaxed the tension in his leg and let his step-son “Fine. Just keep it in your pants.”

“That’s a weird way to say thank you.” Shaun grumbled before he started massaging Nat’s foot.

Nate watched nervously as Shaun picked up his foot. Nate had always hated being tickled even as a kid. Shaun had suddenly tickled him out of nowhere, maybe just to torture the already tortured and feminized man. Or worse, maybe Shaun was a lot more like his mother than either of them realized. Sarah wasn’t particularly affectionate most days but one night as they were getting hot and heavy she discovered just how ticklish he was and some wild immature spark was set off inside of Sarah as she tried to attack his sides until he was begging for her to stop. Even Sarah’s admittedly great rack on full display could not salvage the evening for him.

Shaun glanced at Emma, and sure enough she was watching him like a hawk. He had no choice but to give Natalie a massage. Of course, Natalie wasn’t Natalie but Nate. A fact he both kept reminding him of and trying to forget depending on the time of day. At this hour, as he massaged the toes he had previously painted the nimble frame of the girl that laid beside him it became hard to remind himself who she was. As she moaned and sighed pleasurably underneath his skillful hands he bit his lip as he tried to distract his mind from the reality of his situation. His mind slowly drifted to the first blonde bombshell he met thanks to his dad.

On his eighteenth birthday his dad told his mom they were going on a boys weekend in Vegas. That was true for the most part, he rented a suite for the weekend, complete with a jacuzzi tub, fully stocked wet bar, king sized bed, and a beautiful blonde with breasts nearly spilling out of her tight little black dress. Patting him on the back and handing a box of condoms his dad smiled. “Happy birthday, kid.” winked, and then left him alone in the suite for the rest of the night.

For the first hour they just talked, something she explained was common among guys their first time when he tried apologizing for being nervous. When he asked how she knew, she explained in her line of work she had to be able to read what clients really want. They talked about all manner of things, her job, his family, how she sized clients up, friends, his failures with the opposite sex. She put her hand on his knee and said, “I’m gonna let you in on a secret. If you want to win any girl’s heart? Get really good at giving massages.” he laughed her off at first before she explained, “If you know how to use your hands, learn…all the right places to touch a woman?” She cooed warmly as she took his hand and placed it on her chest over her heart, “They’ll be eating out of the palm of your hand and cum…back begging for more.”

Shaun listened and learned and massaged her feet, her legs, her back, just happy to be able to touch a woman in real life that looked like she stepped right out of a porno. It wasn’t entirely lost on him that she might have been using him to just get a free massage but between the naked woman underneath him that night and the sounds of ecstasy emanating from her he didn’t really care too much. Between her satisfied groans she would instruct him where to apply pressure and how much. If he deviated from her instructions to grope her naked breasts she would slap his hand away and make him sit in the chair beside the bed. When he complained she would smirk and plant her bare foot into his crotch and gently rub the prominent bulge hidden underneath, “You must taste bitter before sweet my young pupil.” She would say simply. “You could jump my bones right now and flop around for five…or two minutes,” She corrected as she felt his cock twitching beneath her foot, “Or you can do what I say and have any woman begging you for more for the rest of your life. Which do you really want? And try to use your big brain for a change.”

“OHHHH!” Nathan moaned, bringing Shaun back to the present as he felt Shaun’s thumb press into his skin and run down the arch of his foot.

Emma truly had gotten caught up in the movie. She didn’t realize until she heard a loud moan from Nate what the two were doing. For a second she was confused that Shaun had oddly enough decided to start massaging Nate’s feet out of nowhere. When she remembered why, she mentally kicked herself. She wanted to torture and humiliate her brother more and rubbing another man’s feet certainly did the trick, especially if his face was any indication. At the time it didn’t occur to her that Nate would enjoy it. ‘Damn.’ She thought bitterly, ‘I can’t go back on it now.’ Emma knew from her father, if she went back on it now it would undermine the power she had only just now seized. ‘I’ll have to figure out a way to take the fun out of it for Nate later.’ She thought as Nate let out another pleased moan. ‘And I’ll have to think of more ways to torment Shaun as well.’ A wicked smile crossed her face as she grabbed a handful of popcorn from her bowl. ‘After all, once Ma’ gets back Nate will be gone from this house and our lives, my fun will be over.’ Crunching a piece of popcorn she thought, ‘But I’ll be able to hold this over Shaun’s head the rest of our lives.’ 

Shaun wasn’t sure just how long Emma expected him to rub Nat’s feet so he went by how loudly she moaned. At first they were audible, but the longer he stretched and rubbed the quieter they got until they were too faint to be heard. Once he could no longer hear them he moved on to the next foot and started the process over again. By the time Shaun had finished the movie was reaching its conclusion. To help himself not brood he kept his focus on the glittery red toenails that he had painted. They didn’t look like manly feet, like the Flinstones or anything, they looked like they belonged to a girl, smooth and freshly painted. He could easily imagine them in a pair of stiletto peep toe shoes. Once upon a time he was able to get his home run with a girl by paying for a visit to a nail salon. Like every girl he had been with he lost interest in her after closing the deal or shortly after and now here he was being forced into a farce of a relationship all because some girls got their feelings hurt and went crying to Em.

When the movie finished it was late enough that Emma declared it was time for bed. Reminding Nate he would have to get up early to start his morning routine. “Lucky me.” He yawned as he sat up, arching his back in a big stretch, not considering how it looked with the fake breasts pressing tightly to the already tight shirt as he spread his arms and arched his back.

“Keep showing off the girls like that in front of Shaun and you’re gonna get lucky.” Emma laughed. Nate blushed and covered his chest despite knowing there was nothing there but padding. Emma giggled, seeing his discomfort, “Knowing you Nat that was the point. Come on, we’ve gotta go over your night time routine.”

“Like what?”

“You can’t sleep in your makeup, it’s bad for your skin.”

“...Oh, right.” ‘At least I get to take this crap off.’ he thought with a smile as he followed Emma into the bathroom. Finally alone Shaun breathed a sigh of relief as he stood up and adjusted his erect penis in his pants and went into his room to take care of it before he slept.

Nate’s nightly routine was similar to his new morning routine; first he removed his makeup with alcohol wipes. He was then given a pink shower cap and made to tuck the shoulder length wig inside. When he asked, “What’s this for?”

“For your hair, silly. You know you can’t wash your hair every day…right?” The blank stare she received answered for him and explained Nate’s lackluster hair.

Embarrassed, he pulled on a strand of the hair, unconsciously wrapping it around his finger. “Why don’t I just take the stupid wig off? It hurts like hell anyway.”

Emma said, “It hurts because you’re not used to wearing it. Yet. We’ll talk to Fredrico soon and see if he has something that might help. In the meantime…scoot, scoot.” She waved him on with a gleeful smile as she sat on the sink counter, showing no signs of leaving. Nate sighed as he started the shower and while he waited for the water to warm he tucked the hair of the wig into the pink plastic cap. Checking the water was indeed hot enough he glanced back at Emma, clutching the towel to himself as he hesitated. At this point she had seen him naked multiple times. Worse…as he thought about the video of him and Shaun. He shook his head and dropped the towel and stepped into the shower, quickly closing the frosted glass door between him and the outside world.

After he showered using the fruity body wash at Emma’s instruction. He patted his body dry before he was given a fuzzy pink robe with large purple and blue butterflies stitched across the robe.  Then he plucked any stray hairs that may have sprung up throughout the day. That done he washed his face, followed by cleanser and moisturizer to his face before doing the same to his arms and legs. All the while completing these tasks with a smile on his face, thanks to Emma reminding him of it and what was at stake if he didn’t follow a seemingly small demand. ‘It’s fine.’ He said, comforting himself as he brushed the wig, ‘Just a few minutes more and I’ll be alone in my room.’ 

Cleaned and finished brushing his hair, he followed Emma into her room to change for bed. “Come on!” Nate hissed at the sight of the satin turquoise nightie, not wanting to possibly attract Shaun’s attention and walk in on him wearing the insanely girly pink fuzzy robe. “Your mother doesn’t dress like that for bed, she wears pajamas. Emma placed the offending garment on her bed. “You don’t even dress like that for bed.”

“How would you know what I wear to bed?” Emma questioned with a look of disgust.

“Don’t give me that look.” He huffed, “I’ve been in the living room when you sneak down for a midnight snack at two in the morning.”

Emma narrowed her eyes on him for a moment as she considered his explanation, “I guess I can believe you. For now.” She added, “We also don’t wear aprons, or heels to clean, or fuzzy pink robes. But you’re not me or Ma. You’re your own person, Natalie.” She added emphasis to Nate’s feminized name, letting the meaning sink in before continuing, “The Natalie I know is a girly-girl obsessed with clothes and makeup…and I guess my brother.” She laughed mischievously. 

‘Don’t be stupid.’ he told himself, ‘I’ll just take it off in my room.’ “I guess you got me there.” He faked a smile, taking up the offended garment and the matching satin panties that were included. The satin material felt oddly pleasurable as it caressed his smooth skin. The panties immediately teasing his cockhead and causing it to throb with pleasure. 

“See, isn’t that better?” Emma cooed at the blushing man.

“It’s…fine.” He lied, to himself, to her, not wanting to admit any type of enjoyment to himself or the wicked witch that tortured him.

All in all the multiple tasks took him a little over a half an hour, as he was leaving he grabbed the fuzzy robe and covered himself with it, deciding it was the less humiliating option to be seen in. Nate hurried to his room as he was beyond ready for privacy where he could strip and sleep naked rather than sleep in…the nightie, maybe even take care of his growing erection to ensure a blissful night sleep. 

At least, that’s what tried to do, instead he ran into the door when it refused to open for some reason. Assuming he had just miss-timed the turn or his hand slipped, whatever the particular cherry was on top of the shit sundae that was his Saturday, he tried again. However the knob would not turn. He turned the knob back and forth and was about to throw himself into the door when Emma stopped him, “Uh, what are you doing?”

“Why’s the door locked?”

“That’s Ma’s room.” Emma said, “After last night’s confusion when you dragged my brother in there to get at his salty treat, I figured it was better to just go ahead and lock the door.”

“Where am I supposed to sleep?” He pursed his lips, already knowing the answer and knowing the couch was not meant for someone to sleep on in any way that was comfortable or restful.

“...I swear you can be a real airhead sometimes. You’re going to sleep in Shaun’s room, obviously.”