I Need You To Feel Again

It wasn’t that twenty-three-year-old Jack necessarily considered himself as a “transgender” or anything of the sort. He simply dressed the way he did to please Alex Gaskarth, his employer. Sure he enjoyed the cute dresses, stockings, cat-ear headbands, and pastel pink collar, as well as other little toys and accessories, but he still preferred his male pronouns he was born with. Although, there was a certain exception for his boss.

Three months have passed, and Jack still works for the Gaskarth residence. He has loved living there and housekeeping the lavish home. He would inspect every room, door to door, corner to corner, and assuring himself that each was up-to-par. He did this all on his own, wearing his cute little Gothic Lolita-style maid uniform, for which Alex had especially tailored for him.

There were a few more rules Mr. Gaskarth had laid out for the young boy after their steamy affair.

“You can’t wear pants anymore, only dresses. Should a guest come to the house, you would go to your bedroom to change into the other outfit I prepared for you, but regardless,” He explained, hot heavy against Jack’s neck. “I want you in only this baby girl, okay?”

Jack nodded, chewing his lip and agreeing to Alex’s terms. He did have a choice honestly, to find a rather “normal” job and avoid cross-dressing. Though, Jack thought it would be a fun experience, and the plus side was that Mr. Gaskarth was hot, and great at sex in Jack’s opinion.

Jacky, as Alex calls him, was dusting a few bookcases and cabinets in the library. He tended each and every shelf accordingly, making sure each was clean. In level to Mr. Gaskarth’s standards. He would be home late tonight, for he had many meetings to attend to, and a very tight schedule. This calmed Jack, because he could take his time in his cleaning. He wouldn’t have to rush himself, and be sure everything was clean before Alex arrived.

He grabbed the step-stool and reached over for the highest bookshelf, clearing them from all of those allergens and dander accumulated from lack of use. He heard the door slowly open, which caused him to furrow his brows. It couldn’t have been Alex, he shouldn’t be home yet. Though, to Jack’s surprise, it was. A very angered Mr. Gaskarth entered his library, shutting his door and walking towards his office chair to take a seat.

Jack swallowed thickly, stepping off the small ladder and walking over innocently towards his boss. A concerned look on Jack’s face as he examined the bead of sweat on Alex’s brow, caused by his frustration.

“Everything alright?” He muttered softly, chewing his lip.

“Not really.” Alex sighed, rubbing his face. “We’ve been losing a lot of money lately due to advertisement issues.”

“I’m so sorry.” Was the first thing Jack could say, not really aware of how he could respond.

“No need Kitty. Just come here.” Alex signaled the boy to his lap, for which he complied immediately.

“Want me to make you feel better?” Jack asked softly, chewing his lip and slowly sitting on Alex’s lap. His legs spread apart on either side of Alex as he faced him.

“You always do.” Alex smirked and rubbed his hands against Jack’s thigh, immediately beginning to suck his neck. “What did I say?” Mr. Gaskarth murmured as he went further up Jack’s leg, feeling lace panties underneath the skirt of his dress.

“Don’t wear anything underneath unless you say.” Jack reiterated one of the many rules set by his boss.

“That’s right Kitty. You knew Daddy was already mad, and you just made him even angrier.” Alex explained, slapping one of Jack’s ass cheeks and biting his lip at the sound of the smacking noise his hand made against the skin.

“I’m sorry Daddy, I just wanted to be cute for once.” Jack murmured as he felt the finger of the older man trace over the waistband of the lingerie.

“Go to your room, now. I want you on the bed. Play with yourself for a little.” He instructed and moved his face to whisper against Jack’s ears. “And you better hope I take a long time to get up there.”

Jack nodded, lifting his leg and slowly climbing off of Alex. He walked over to the door, looking over at Alex with an almost saddened look. Then slowly leaving the library.

It wasn’t that Jack didn’t like the relationship he carried with Alex. He just felt more like play thing, then someone to love. It was as if Jack wasn’t a human anymore, with emotions and need of some sort of affection. He loved working for Alex, he really did. Yet, there was something that ached in his chest. The want for attention other than sexual pleasure. He was young after all, and he had his entire life to look forward to. He didn’t plan on staying with Mr. Gaskarth for too long. Jack was better than that. He didn’t want to be paid to be a cleaning boy/sex slave. He wanted to be married, have kids, and lead some kind of normal life. Don’t get Jack wrong, he did like Alex, a lot. Though the possibility of having some other life other than spreading his legs for him was obviously impossible.

The boy entered his bedroom, keeping all of his clothes on beside the lace pink panties Alex let him wear on occasion. To Jack’s dismay, this day was not one of them. He knew his routine, grab the bottle of lube and begin to stretch himself for Alex. He couldn’t touch his aching cock, because if he was caught the punishment would be far worse. Jack doused his finger, more than he is accustomed, laid himself down on the bed and spread his legs. He lowered his hand to tease himself, by pressing one of the pads of his fingers against his entrance. Eventually, he pushed his finger in. He sucked in air, and relaxed. His eyes darting towards the door and hoping Alex would come in soon. He pumped that finger inside himself over and over, moaning a little when he wiggled it towards that pleasing spot inside of him. The second finger came in shortly after, causing Jack to throw his head back. He moaned pleasantly at the feeling. His eyes slowly slipped closed, then he bit his lip as thoughts of Mr. Gaskarth fucking him into the very mattress he lay upon swarmed his mind.

“Good girl.” Alex praised beside the bed, rubbing the boy’s thighs as he watched him finger himself. Jack’s eyes opened up again to see Alex, partially clothed and with a sick smirk on his face. He traced his hand up and down Jack’s shaven legs, caressing the soft and supple skin the boy bare.

“Take ‘em out.” He ordered, and chewed his lip as he watched those long fingers exit Jack’s stretched entrance. Alex ran his hand through Jack’s hair, pushing the boy’s fringe out of the way so he could see the boy’s eyes.

“Daddy, am I really really in trouble this time?” The younger male pouted, eyes blown and staring into Alex’s own.

“Get on your knees.” Alex stated, completely ignoring Jack’s question.

Jack knew Alex was angry, but not necessarily at him. The anger was geared towards his job, and all the stress it has caused the young CEO. He knew he was just using Jack as a form of stress relief. Almost as if he were pretending to be angry, and using any excuse to be irritated and punish Jack.

“Suck me off, baby. I want you to swallow like the good little girl I know you are.” Alex motivated the younger boy, and watched as the boy slowly lifted his hands to unzip Alex’s pants. His eyes adverting the aching cock that sprung out before him, and were instead focused on his boss’s gaze. “Don’t touch yourself. You had your fun.”

“But Daddy, I didn’t get-“

“What did I say?” Alex interjected, his brow furrowing in frustration.

“To suck you off.” Jack’s eyes lowered, feeling as if he failed and legitimately angered Alex.

“Then? Don’t speak, suck.”

Jack nodded with an ashamed expression, swallowing back his words and other emotions and thought just pleasing Alex and nothing else. He licked his lips and cleared his mind, reaching for Alex’s length then looking up with innocent eyes. He brought his mouth closed to the tip, and lightly licked it. His eyes never leaving Alex’s own brown ones. He repeated that action for a few times, then put the tip into his mouth. He hummed when he heard Alex moan, causing those sweet vibrations to go through Alex’s body.

He slowly bobbed his head, eyes focusing on Alex as much as possible. The looking down at the other man’s naval as he continued to move his head. He was slightly enjoying himself, the humiliation and innocent act he played for Alex. It was like a game of some sort. To please himself, he pleased Alex. Even if it meant dressing like a girl, and having Alex using the female pronouns as well as derogatory slang.

“Pretty mouth baby.” Alex moaned as he tangled his fingers into Jack’s hair, and guiding him to a quicker pace. Jack hummed in response, sucking faster and harder as he did so.

The more the boy’s head moved against Alex’s shaft brought the older of the two closer to orgasm. Jack had immensely improved on his sucking, and deep-throating Alex’s length whilst carrying an innocent aura. How he did it, Alex hadn’t a clue. Nor did Mr. Gaskarth care to question the boy’s ability of appearing so virtuous, despite the aching cock he was gagging around.

“God Kitty, look at you so… ah- enjoying that cock in your mouth, hm?” Alex groaned, running his hands through Jack’s hair to get a better look at him.

Jack pulled off, pumping the dick covered in his own spit and kissing the tip. He pecked it a few more time, before responding to Alex’s dirty remarks. “Yes Daddy, you should come in my mouth.” Jack smirked, licking his lips then pumping the brunette’s dick even faster. Then he continued to suck on it a few more times, realizing Mr. Gaskarth’s nearing the end. He moaned, stuttering out the warning and eventually coming into Jack’s mouth. He looked down to see the boy take it all in, without swallowing like he was taught. Once Alex finished, Jack brought up the come. He showed Alex it was in his mouth and played with it, then moaning before he swallowed it down.

“My little princess.” Alex sighed, rubbing Jack’s cheek then looking down at his crotch.

“Daddy, I’m still hard.” Jack whined, pulling up the skirt of his dress. Just above his stockings to reveal his painfully hard cock.

“You’ve been a good girl.” Alex acknowledged, sitting on the bed and slowly stroking himself although he was still sensitive. “Lie down, and I’ll take care of you.” Jack nodded obediently, laying down next Alex with ambient eyes.

Mr. Gaskarth grabbed the lube, lathering his fingers and licking his lips. He watched as Jack spread his legs, lips pressed together and ready for him.

“Let’s get that pretty pussy of yours stretched out for me baby.” He suggested as he pressed to fingers against Jack’s entrance, and pumping the vigorously. He avoided Jack’s spot on purpose, causing the boy to whine angrily. He looked down at him at muttered a small, “Please Daddy, m-more.” As he shifted his hips.

“Patience baby girl,” He smirked. “I’m only getting started.” He said, admiring the way his third finger slipped in with ease. Jack moaned again, throwing his head back and making soft noises.

After a few pumps of his fingers, Alex replaced them with his cock. He pressed the tip and slipped it in, immediately fucking into Jack quickly.

“Fuck Daddy!” Jack moaned loudly, back arching immediately at the sudden pace Mr. Gaskarth set.

“I know you like fast and rough.” Alex groaned and lowered himself to kiss Jack’s neck and lightly suck on it.

“I know you like when Daddy fucks you hard and fast with his cock.” He boasted, jerking his hips faster and trying to get himself deeper inside of Jack. The moans were uncontrollable, and almost not there. They passed Jack’s lips as “Ah, Ah, Ah,” and the few small “yes’s” in between.

“Daddy, Ah- Ah. I’m gonna come!” He practically skrieched out, as he his dick twitched and spewed his orgasm, covering the two. The involuntary tightness caused Alex to reach his limits as well, and came deep inside of Jack. He stalled his hips, and let the come shoot way inside of Jack, then eventually pulling out and watching it drip out of Jack.

“Fuck…” Alex groaned and lifted and laid himself down next to Jack. He used his finger to pick up the Jack’s come, and bring them to the boy’s fingers and watch him suck them clean.

“Pretty girl, like the taste of your sweet pussy?” He teased, and Jack nodded after popping Alex’s fingers out his mouth.

The remained in silence for a while, catching their breaths and thinking of each other. Alex thought about Jack, in a different perspective though. He’d always seen him as an object to fuck, and fulfill every sexual desire he dreamed. Not this time. He didn’t want Jack to feel that way in anymore. The soft and sullen look in the library gave him the jist of Jack’s overall disposition.

“Jack, I want you to be my boyfriend.” Alex murmerd, turning his head and looking over at Jack.

“Wh-what?” Jack scrunched his face, dazed by the fact that this was reality and not some sort of dream he was having.

“I want us to be more than just, this. I want to take you places, show you the world. I want you to be happy with me. Our sex is great, but imagine all the other things we could do together. You make me happy, and not because of the sex. Your overall person brings me joy.” Alex admitted, a soft smile on his face.

“I-I uh, yes. Okay, I will.” Jack replied hesitantly, almost unsure if Mr. Gaskarth was being serious or not.

“But there still one more exception.” Alex smirked, turning his body over and resting his head on an arm.

“What?” Jack quirked a brow, uncertain.

“You’re still not allowed to wear pants, princess.”

Notes

So, just a short little sequel to Camisado, because I hadn't written anything in such a long time. I've been so busy with school and such, but found some time to write something short, sweet and simple. I hope you enjoy!