tagTransgender & CrossdressersSomething Better Ch. 03

Something Better Ch. 03


A.N. Well the moment you've all been waiting for is here. I hope I made it worth the wait :D

The following contains: Sexy happenings between a top dick girl and a bottom boy. If you're not into that kind of stuff, then you're missing out bruh.

I hope you all enjoy! Happy fapping!

Chapter 3: Take It


'So tomorrow at three would be okay?' Casey read the text as discreetly as possible since he didn't want to be blatantly texting at the dinner table.

It was Friday night, so he and his parents had just sat down together for supper, but Gabbi had been texting him for a few hours now trying to work out plans for their next anticipated encounter. Over the last few weeks, Casey and Gabbi had been meeting up as often as they could, enough so he was able to officially label it as 'boyfriend/girlfriend dating.' They were always able to see each other on the weekends, but their time together on weekdays was limited since Gabbi had to work and Casey still had school. Still, they managed at least three or four dates a week.

As long as you could call Gabbi insistently teasing the poor boy to the point of insanity a date. Not that he was complaining, of course.

His phone rested on his lap as he casually shifted his arm under the table to reply.

'One sec, lemme just triple check with my parents.' He sent the message then immediately looked up to the other two bodies at the table. "Hey mom, are we doing anything special tomorrow?"

Casey's mother Mia Bennett was a bit of a bombshell. She had long wavy blonde hair, big blue eyes which matched his own, and a body that had been making dicks hard for years. She looked at him in between bites of her food and shook her head, "Mmm, mmm. I don't think so. Your dad's got work but I don't have any plans. Why?"

He tapped his fork against the glass plate thoughtfully. He needed to be cautious about this. If his parents knew he had a girlfriend they would probably want to meet her or at least know more about her. And Casey didn't think either himself or Gabbi were ready to do the whole 'meet the parents' thing. They had only been dating for about three weeks now anyways. So he needed to come up with a proper excuse for him to get out of the house tomorrow and be gone almost all day.

"Well, my friend in class needs help with studying for final exams. She doesn't wanna hire a tutor or spend time after school with teachers so she asked me for help. I was wondering if I could go over to her house tomorrow and help her out." His formulated the lie in a matter of seconds and hoped his parents bought it.

"She?" His father spoke, apparently, that was the only word he caught throughout the entire statement. Casey's dad Thomas was a rather simple man, with a lean but slim build similar to his boy's. With dark hair and dark eyes, he came across as the average Joe type. Like father like son, he often thought to himself, only Casey seemed to catch more of his mom's feminine genes rather than his own. He counted himself lucky every day for slapping a ring on Mia's finger; there was no other milf he'd rather spend the rest of his life with. "You're gonna be going to a girl's house, who is not Jessica, to 'study'?" He did air quotes over the last word.

Casey rolled his eyes. "Yes, and her parents already said yes, so can I go?"

His dad shrugged, "As long as you wear a condom."

"Honey..." Mia spoke up with a chastising tone, he could be a very sarcastic man and she was thankful that her son didn't pick up too much of that trait. "Is it close by?" She asked.

"Yeah, it's like a fifteen-minute walk from here." He replied. "She lives in the Sea View apartment complex. She wants me to be there tomorrow at three in apartment #304, now you know so you can come get me in case she tries to murder me."

"Okay, maybe he did pick up his father's sense of humor." She thought, flashing a heart-melting smile. "It's okay with me, just make sure you text me when you're there and when you're leaving."

He did an internal fist pump at that, "Thank you! She's gonna be really thankful."

"And use a condom." His dad once more interjected.

"Tom!" They both laughed.

Casey blushed, however. "Well...if it comes to that, I don't think I'll be the one wearing it..."

Now with the go-ahead from his parents, he sent another message to Gabbi, 'Yup! Tomorrow at three is good :)'

His family continued eating and making more small talk about who this mystery girl was, but Casey mainly tuned it out aside from giving the occasional little white lie answer. If they knew that Gabbi was a full grown woman inviting him to her house, they might've been more apprehensive about giving him the green light. So he told them she was in his Algebra two class and they had known each other since the start of the year. He just didn't talk about her because they were only friends. Both Mia and Thomas seemed to buy his story while they ate.

A few minutes went by before he felt his phone vibrate on his knee.

Her message read, 'Yes! Finally lol.'

Casey grinned and excitedly texted back again, 'So do we have any ideas of what we're gonna do?'

Seconds later, 'Sweetie, I think we both know exaaaactly what we're gonna do ;)'

Immediately his heart began to pick up speed. The couple had already practiced with sexting each other. Gabbi was essentially an unstoppable horny force, and when they couldn't be together all the time, they liked to pretend to be. The day after their experience at the cafe, she practically walked him through how to masturbate with her panties over the phone. Before he met her, Casey didn't think he was into a lot of kinky things. Gabbi was definitely broadening his horizons more and more every passing day. Man, how his world had changed.

So feeling a bit daring, Casey replied to her with, 'Oh? Why don't you refresh my memory for me?' He formed a tiny smirk after he hit send and took a few more bites of his meal.

Within a minute he felt it buzz, 'You're gonna finally show me that cute little butt you've been hiding this whole time.' He had to fight back the desire to giggle at that. This flirty texting was a very welcome change from what he was used to. Compared to his text conversations with Jessica, the only time they ever got sexual was when she requested the dick pic that ended the relationship. So needless to say, his coy texting with Gabbi was a complete turnaround from his previous experiences of sending naughty messages back and forth with a girl. There was another buzz from the phone, 'Plus with all those tight hip hugging pants you've been wearing, that ass has been practically begging for a good spanking. Lol'

That time he had to bite his lip to prevent himself from laughing, he hardly considered himself the attractive type. Again the words 'below average' echoed in his head. But Gabbi was so attracted to him, her confessions of lust for his body were definitely sparking up the tiny embers of his confidence. That spark summoned the boldness within him to text her back. 'Really? You gonna bend me over your knee like a bad boy? Punish me for teasing you with my ass? ;)' Never in a million years would Casey have sent such a racy message before. He was too shy, too afraid of rejection. But now look at him, sending pervy texts with a semi-confident attitude, eagerly awaiting the reply. All thanks to his new relationship with Gabbi, she was amazing.

But right after he tapped send on his phone, he heard his father slyly say, "And what're you so smiley for?" Casey quickly looked up to see his dad eyeing him with a snarky smirk.

"Nothing!" He shot back, far too quick for it not to sound like a lie. To his right, his mom was giving him a much similar look, one that told him her mother's intuition was seeing right through him.

"Are you texting her?" She asked innocently.

Casey felt his face heating up, "No. I mean...yes but I'm-" His phone buzzed again and he froze, both of his parents still staring at him knowingly. The message was of course from Gabbi and the thought of what she sent and the possibility of his parents wanting to know what it was made him feel like a heart attack was imminent. "...May I be excused?"

He couldn't have gotten out of there fast enough. After his parents gave him the okay to leave the table he scurried away as quick as he could. He fled the kitchen and headed upstairs to his bedroom, all the while hearing the teasing remarks of 'aww our son's got a new girlfriend' behind him. Hastily Casey flew through the hallway, shut his bedroom door behind him and threw himself on the twin sized bed in the corner. He didn't even bother to turn the light on. His room was rather small and cluttered, a stereotypical boy's room with a computer desk, small TV at the foot of his bed, and blue wall paint. A bit messy, but it was home.

He quickly lifted his phone to his face. His eyes were again lit up by bright white screen as he read her next text, 'You know that I will sweetie. I think I'll need to spank you twice as hard for teasing me right now.'

The grin returned to his face while he texted back, 'Oooouu, I've never been spanked before. But the thought of you punishing me like that is a huuuuge turn on.' He finished the message by sending the 'heart eyes' emoji.

She replied again in a matter of seconds, and Casey figured that she was probably also relaxing at home while texting him. 'Oh believe me baby, I'm hard as a fucking rock thinking about it. Lol.'

Casey bit his lip, 'So do something about it...' He was getting very horny already as well. Silently hoping they would begin to 'sext' again, his free hand absentmindedly slid down his body to the front of his pants, pawing at the smallish bulge steadily beginning to press against the fabric. Something else that was entirely new to him was that he'd never thought that the image of a beautiful woman with a hard cock would excite him. But it made him horny as Hell so he accepted the apparent fetish gladly.

The next text came a bit slower than the others, it took maybe half a minute for her to reply. 'Strip.' His hopes were confirmed. Whenever Gabbi texted him that, he obeyed with glee, because that meant they were about to play. He practically threw the phone to the side in order to hastily begin removing his pants. It was a liberating feeling, being able to express his sexuality with his girlfriend rather than being afraid to.

Almost comedically his clothing flew off of his body, shirt, shoes, pants, socks, undies, all were tossed as far as possible, smacking into the wall across from him. A now butt naked Casey plopped himself onto his bed again, semi-hard cock bouncing with him. Phone in hand, he mashed away at the buttons sending his next text. 'Okay, now what babe?'

Now that they both were doing nothing else, just waiting for each other's response, the texts were able to come much quicker. 'Lick your hand, think of me and start tugging boy.'

Casey did exactly that, giving the palm of his hand a quick lick, moistening the skin. He then spread his legs to reach down and start jerking off. He took his smallish cock in hand and began squeezing the hard flesh, pulling on it and tugging as he was told.

Another text came before he could reply, 'So, how does my cock compare to yours babe?'

He giggled at that and shifted his free arm around to text one-handed. 'Playing with yours is soooo much more fun. It's so big and thick.'

Images of her with her skirt hiked up flooded Casey's thoughts, her huge, veiny dick flopping down out of her panties and landing on his face. Its thick, enticing aroma swimming into his senses, and his tongue poking out to get just the slightest taste of her delicious meat.

'You gonna be ready for it tomorrow?'

Casey nibbled on his bottom lip, the thought of seeing her lady hood in the flesh again tomorrow being all he could picture. 'I hope so, will you be gentle with me?'

He could almost hear her trademark sultry laugh accompanying her next text. 'With the way you've been teasing me? Absolutely fucking not ;D' He laughed at that, 'I'm gonna stick this fat cock all the way in your ass and you're gonna like it bitch.'

"Oouu..." Casey cooed aloud, once again, him and Gabbi discovered a fetish that he had dormant within his psyche. Degradation. Apparently, being talked down to was a lot sexier when Gabbi did it to him in a bedroom-esque environment. Or any type of pet names really did it for him, baby, good boy, sweetie, bad boy...slut... as embarrassing as it was, they all sent a charge into his genitals that had him at her feet, ready to worship her.

Although he hadn't really gotten the chance to worship her in the same way he had outside of the café. When he gave his first blowjob ever.

He'd been yearning to give her his second one...and maybe a third...forth...fifth, but the opportunity hadn't yet come. Aside from Gabbi's teasing and flirting, the majority of their dates had been getting to know each other more.

Like just a few days ago, he learned that Gabbi's favorite color was indeed red!

...And her favorite position was pile driver...

'Mmm...yes Mistress.' Casey texted, now fully jacking the boy cock in his hand. Squeezing and twisting the pale flesh hard.

'(Fuck I love it when you call me that.) I'll bend you over my bed...spread those soft ass cheeks apart, and squeeze my cock into your tight virgin little hole.'

The conversation continued, Casey playing with himself the whole way.

'Oh please Miss...please go easy on me...' He played up his, poor defenseless persona that he knew she loved.

'Shut your mouth slut. *crams my panties into your mouth*'

'Mmmm! *whimpers and pushes back into you*' Casey thought for a moment to go and grab Gabbi's actual panties that he kept with encouragement from her. But he was too wrapped up in the moment to want to walk away from jerking off.

'*I start bucking forward, driving my dick inside you hard* That's right boy...take it like a good whore...'

Casey bit his lip, his hips thrusting upward into his hand. The pleasure and desire for release driving him to jack his prick harder.

But as he was in the middle of his next reply, suddenly there was a knock on his bedroom door. "Casey honey?" The voice of his mother softly called from the other side.

He jumped so high he was sure he almost hit the ceiling. His cell phone slipping from his fingers and falling onto the blankets under him as he quickly grabbed the sheets and pulled them up to cover his body in a panic.

There was no lock on his bedroom door, if his mom decided to open it she would see him spread eagle on the bed, jerking off like a horny pubescent teen.

Casey's eyes frantically searched his room for something else to cover himself with and eventually they fell upon his shirt. It was the only article of his clothing that was within reach without him having to get out of the bed. So he leaned over the edge and snatched it off the floor, throwing it over his head, sticking his arms through the holes and situating himself back beneath the blankets. He cleared his throat, "Yeah mom?"

"Can I come in? I wanna talk to you." She said sweetly.

"Ugggghhhhhh." He mentally groaned, but vocally he said, "Sure! Come in." For a second he panicked again as he didn't want to look like he was just sitting there not doing anything, so he fished around in his blankets until he found his phone and brought it up to his face pretending to be texting.

The knob on the door carefully turned and as the door pushed open, the big blue eyes of his mother peered in to the darkness of Casey's room. "Hi baby." She said stepping into his room and shutting the door behind her.

"What's up mom?" Casey asked, making sure to keep his lower body slightly turned away from her to hide his prominent erection.

Mia offered him a heart melting smile and walked right up to beside his bed, she was still dressed in her blouse and skirt from dinner so he figured she and dad hadn't gotten ready for bed yet. "Well, I wanted to talk to you about...this new friend of yours."

Casey rolled his eyes, "Mom I told you, there's nothing to worry about, we're just friends."

"No honey, that's not what I mean." She turned around and sat herself beside his laying form.

The teen had to gulp when he felt the pressure of her butt coming down and tugging the blankets against his still hard member. "Oh God."

His mother sighed, "Listen, I know how much Jessica hurt you. And I don't want to see you getting hurt again." She said unexpectedly. "When you first came home and told me you had a girlfriend, I was so happy for you that I didn't even think to tell you about how mean girls your age can be."

The phone in his hands was moved to the side as this unplanned Mother Son deep conversation started, he felt it deserved full attention. "Mom..."

She brushed a lock of blonde hair over her ear, "If you are really just friends. That's okay, but you and Jessica were 'just friends' at first too. What I'm getting at here Casey, honey is...I guess I just want you to be careful. I don't want you getting hurt again, my heart breaks every time I think about it."

At this point Casey would've sat up, but he was still being conscious about his nakedness below the blanket. "I'm okay mom. Really, Jessica and I broke up almost two months ago. And again, I reiterate that I'm only visiting a friend to help study for finals. Nothing more I promise." He felt a little bad about lying to his mother when she was trying to be heartfelt and such.

Mia shrugged, "Okay if you say so." She then leaned over and kissed Casey on the forehead, "I only want what's best for you, and I want you to be happy. So...yeah...I guess that's it." She paused, sharing an awkward moment of silence between them. "I probably should've prepared a better speech before I came in here. It started out better in my head, I wanted to talk to you about being safe and like...you could tell me anything and stuff and...yeah..."

Casey laughed, "Hey, you did better than dad."

The two giggled at that and Mia stood up off of his bed. "Oookayyy, I'll leave you alone now. To...text her?" She hinted at.

"Yeeeesss motherrrr I am texting her. That doesn't mean we're gonna get married." He joked as she stepped away from his bed and over towards the door.

"Well hey, if she picked my son to marry that means she's got good taste so I'll give her that." She took hold of the doorknob and cast one more look over her shoulder. "Okay Casey...real talk. Just between you and me...is she really just a friend?"

There it was, probably the real reason his mom came in here. To try and suck more information about his mystery lady out of him in the vein of a heartfelt conversation.

This time when Casey groaned, it was out loud. "Ugggh! If I tell you will you please stop talking about it?"

She released the door knob, suddenly looking much less serious and more like an excited child, "Yes!"

Casey sighed, "...She...I think she's...pretty. Interpret that however you will that's all you're getting!" He finished with a wave of his hand, "Now begone from my domain!"

"All I needed! Thank you!" Mia spun on her heel and practically danced through the door, "I love you honey!" She said before shutting it.

"Love you too mom." Casey replied irritated. His mother was harmless, but was a sucker for info on his personal life. She always treated him like a golden child because he was their only son, which most of the time he enjoyed. But when it interrupted his sexy texting with his girlfriend, it came off as annoying. So he quickly re-opened the text chat with Gabbi, and saw that she sent him another message waiting on a reply.

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