Scene 26

“I can’t believe you are making me do this.” Jackson said standing in his living room, hip cocked to the side as he looked down at himself with a disgusted look on his pretty made up face. The bathing suit, the bikini, had a tube top that had a cut out between his breasts. Pressing his lips together at the side of his mouth Jackson corrected himself that they were his… but they were his fake tits. The glue holding them on was holding strong and the concealer made to hide tattoos did an impressive job of hiding the seams, still the little tube top bikini with a thin string going from it to around his neck did little to conceal himself. The chest may not have been real, but he was positive no one looking would know that. He had stared at himself in the mirror for a few minutes to make sure nothing looked out of place and even knowing he was looking at himself he could still feel himself feeling turned on.

It hadn’t been the first time he had started to get hard looking at himself in the mirror, the blonde knockout with the D cup breasts wasn’t how he pictured himself even if it was now how he looked. In the mirror he saw a sexy blonde woman, not his normal brown haired lanky self. Jackson had to turn away from the mirror, getting hard was an exercise in frustration. In the bikini bottoms he looked flat as any girl, his balls pushed up inside of him and his manhood tucked tightly between his legs. Out in the living room now he glared at his older sister who had on a light purple bathing suit on, but had much of it covered. Whatever bikini bottoms she wore were covered by a pair of jean shorts that showed almost all of her legs and a long sleeved white button up shirt that had enough buttons left undone that he could see the hint of what she wore underneath.

Giving her little sister a small smirk Madison pointed at her, moving her finger up and down. “I am not making you do anything. You said you wanted to go to the bar I talked about that was doing some jello wrestling that Callie and I were planning on going to. You wanted to unwind and that is exactly what we are going to do… but you really should put something on over your suit.” She had helped her brother put on his first pair of panties, or at least the first pair he would admit to ever wearing, she very much doubted he hadn’t experimented before considering how he… she really felt. Still looking at Jacqueline it was hard for her to see her brother Jackson. The corset training and diet seemed to be having the effect Jacqueline wanted, her chest was fake for now, but she both walked and sat most of the time straight back, with shoulders back and chest out. Her little brother, now looked like an attractive woman that walked with a wiggle and had even dramatically changed her appearance by going blonde. “I’m not even sure why you are acting upset, that bathing suit looks incredible on you. The men will be drooling, and you wanting me to buy all your drinks tonight won't even be a small problem. I’m betting the two of us will have them climbing over one another to buy us some drinks.”

“I am not taking that bet.” Jackson said as he crossed his arms before forcing himself to put them back down as he noticed his faux womanly chest lifted and was pressed together from the action. The feminized man knew what he looked like and was sure his sister knew exactly what she was talking about. “I could really use a drink though.” He huffed, not thinking about his personal promise to not drink after the hangover he had earlier in the day, but at least had the mental fortitude to resist reaching for some of the pills.

“A drink, that much I can promise you will get. We will be at a bar after all.” Madison said her smirk still firmly in place, hoping her sibling would take the stick firmly up her butt out and loosen up so they could have fun.

Turning to go back into the bedroom he now shared with his friend, a thought hit Jackson, so with one hand on the door frame to the room he turned to look at his sister. “Did you really plan to go to a bar with your girlfriend on her night off, from working at a bar?”

“Hey! It was Callie’s idea, she wanted an excuse to see me in a bikini.” Madison said as she struck a pose, ignoring the fact her swimsuit was currently covered.

Rolling his eyes Jackson proceeded into the bedroom to find something to cover his way too exposed body. In the end Jackson put on the singular pair of pants he currently owned, a spike of joy had overtaken him when he pulled them from a drawer, a genuine smile coming to his face, something much brighter than the small practiced smile he wore at work, though it faded when he put them on. They weren’t real jeans, they were more of a stretchy material that was similar to jeans, but this pair was just a few degrees away from being painted on, still… Jackson wore them, they at least covered his legs unlike most of his clothing. The options for a top weren’t to his liking, not that women's clothing was something he enjoyed at all. He thought, lying to himself, knowing full well how much he joyed the feeling of the soft fabric holding his dick when it wasn’t tucked away or the caress of nylons. Instead of taking something from one of the drawers that Lincoln had emptied out for him, Jackson stole one of his friends' shirts that had a nineties cartoon character on it that he vaguely remembered, but was sure Linc could tell him all about. Pulling the shirt down Jackson bobbed his head a bit from side to side happily, congratulating himself for wearing a proper piece of clothing for once. Lincoln was about four inches taller than his five foot six and while his friend had wider shoulders the shirt wasn’t that much bigger or so Jackson thought, as he tried to adjust the slightly stretched out elastic collar on the old shirt to keep the bathing suit's string strap covered. Looking in the mirror one last time Jackson let out a sigh, as he asked himself once again, why he was letting his sister drag him along to a place where he was going to not just be in a bikini, but also in public.

“I swear you take longer than Callie and me put together when you are getting ready. Hurry up!” Madison said, sticking her head into the bedroom, her little smirk of a smile growing when she saw her sibling wearing her boyfriend’s shirt.

“I do not! I have been in here for six minutes max.” He snapped back, but then looked over his shoulder and over to the bed where he had thrown more than a few articles of clothing that he had rejected when his sister pointed to them as she raised an eyebrow, giving him a knowing look.

“Try twenty, but I understand. That understanding though is limited.” Madison looked down at her wrist before tapping it, pretending she had a watch on. “We are on the clock.”

‘Nag, nag, nag.’ Jackson thought, not believing his sister at all, that twenty minutes had gone by, but also sure in his quest to not look like a bimbo with his office wear had taken up a little more time than he had planned. “You know, I’m going to enjoy throwing you into a pile of jello.”

“Now that is the spirit!” Madison said she hadn’t been really looking forward to wearing a bikini out in public and wrestling in jello for the amusement of a bunch of drunk men. Callie had told her how it wasn’t for them and it was their prerogative to do fun stupid things while they were young. How years from now they would both remember rolling around in jello together, but that wasn’t going to be the case. Their on again, off again and currently on again relationship had a lot of upsides. She thought her blonde sexual partner was incredibly hot, and way more adventurous than herself. Callie does things like sky dive, go parasailing and climb mountains, things Madison couldn’t really see herself doing. Going out and having fun was one thing, but her girlfriend made her step out of her comfort zone, like tonight's event. One of their only points of contention was that Callie just didn’t get being bi, but at least she seemed more accepting of it this time around. Callie had come with her to the mens club with the men dancing around naked and had even put in effort to enjoy herself, so going out for some jello wrestling was the least Madison thought she could do. Her girlfriend couldn’t make it, but Madison was sure she would enjoy a video of the night's events. The playful smile on her face faded slightly as she looked at her new sister and reached out and gave her biceps a light squeeze. “Thank you for coming with me tonight, I know a lot of things are new to you right now, but tonight is new for me too and I think it will do us both a lot of good to get out of our comfort zones.”

Feeling a bit deflated Jackson huffed. “Stop that, I’m trying to be mad at you, I deserve to be mad at you and to put you in a headlock. Stop bringing feelings into this…” He was still mad at her, but in that moment he could see his sister being ****. Jackson didn’t fully understand why he was suddenly overcome with emotions that made his eyes water, but chalked it up to having empathy for his sister after they had planned this together.

“A head lock? Wow, some big girl talk right there.” Madison laughed as she started to turn and head out of the bedroom so the two could make their way to the bar.

The bar itself was little over a forty minute drive to Daytona Beach from central Florida where they lived. It was a two story building that was built up off the ground so that it wouldn’t flood when hurricane season came to the state. Inside Jackson found the place not crowded as such, but had plenty of people already drinking and staying clear of the center of the room where space had been made. Pool tables had been pushed off against a wall to make space for tonight's events and considering he had to walk up stairs to come inside he wasn’t sure how the owner even got them in here other than with a herculean effort. The center of the floor itself was covered in a bunch of pool floaties, the kind people could lay on and lounge in a pool and a pair of inflatable pools filled with more jello than he had seen in one place before. In one pool there was green, lime jello and the other red, cherry jello. “How did they do that?” Jackson asked moving closer to the pools when he noticed it wasn’t just a bunch of jello tossed into the inflatable pools, but it looked like it was made in them.

“I would imagine they used their walk-in fridge.” Madison suggested, thinking it was a bit obvious and wondering if Jacqueline had bleached her brain along with her hair, but she held her tongue.

Soon as his sister said it, Jackson felt a bit embarrassed by not thinking of it before he spoke, but instead of looking a bit sheepish he only narrowed his eyes and glared at his older sister because of the tone of her voice. Her earlier comments about being a programmer while he was just a secretary fetching coffee coming to mind. Instead of snapping back he pressed the ball of his heeled foot on one of the inflated pool things. This time instead of saying his question out loud he considered why they were there. Coming to the conclusion that they would be a lot softer than the bars hard floor for the rough housing. “Huh… smart.”

Giving Jacqueline a sideways glance Madison nodded, she didn’t really think putting the inflatable pools in a fridge for hours to have jello in them was exactly smart. It would make the refrigerated rooms unusable till the jello had set, but it wasn’t worth arguing about. “You stay here, I’m going to get us signed in.”

“Sure, sure… get me a rum and coke!” Jackson called out as his sister walked away. Looking between the two pools it occurred to him that he didn’t know how any of this worked. If there was a line up and he would have to wrestle one girl after another till he came out on top or if they just had two matches. Bending over like he had done tens of times at the office, bending at the waist Jackson stuck his rear out as he tapped the red jello with one of his long nailed fingers so he could watch the red semi-solid wiggle. The smile he often had plastered on his face went up a few notches in volume as he watched his touch ripple out, but it quickly changed as he felt someone slap him on his ass. “Oh!” Jackson yelped as he almost jumped out of the white heels he was wearing. It wasn’t close to the first time his sister had slapped his rear or goosed him, it wasn’t even the first time this week and he was ready to toss her in the pool right now, but as he spun around he found himself staring up at one of the tallest men he had ever seen that wasn’t on a basket ball court.

Off to the side of the room, sitting on a stool at the half countertop that ran along part of the bar, Austin a man of tall stature nursed his bourbon, a large smile coming to his lips when he saw a pair of sexy girls, one brunette wearing short shorts and an untucked button up shirt that showed plenty of cleavage with a pair of flip flops and a blonde wearing an oversized t-shirt, a tight pair of jeans and white heels coming into the room and stand by the pools that were going to be used for the girl on girl wrestling. When the darker haired girl went off to the bar he stood up, and with **** enhanced courage made his way over to the pretty little thing, his pulse starting to race when she bent over and wiggled her little ass in his direction, the tight pair of pants hugging her rear perfectly. “Mmmm” The sound escaped his lips as he gave her rear that she wiggled in his direction a light slap, just like he figured she wanted.

“HE…” Words failed Jackson as he had to crane his neck to look up at the man, the loud HEY he was about to say dying on his lips.”

“Hey yourself beautiful. I saw you butt dialing me and had to come over.” Austin said with the cheesy pickup line, the **** in his system was just enough for him to think he sounded suave.

“Did… did you just…?” The incredibly tall man was so close to Jackson that it brought his mind back to being in the office with Mr. Dunn and along with it the same feeling of being ****. Jackson could feel his heartbeat quicken as he look up at the towering man that was way to close.

“I was just saying hello, how about you come with me and sit your fine ass in my lap as we get to know one another?” While Austin was genuinely asking the girl to come over with him, he was already acting as if she said yes as he stepped closer, running one hand down her back, lightly touching her spine before his palm gripped her shapely rear end.

“My… my sister… she was getting us drinks and… AH!” The sentence ended with a higher pitched noise as Jackson felt the large hand touch him and he felt like he was going to start to hyperventilate.

“I’m a big guy, there is room enough for both of you on my lap.” Austin said, chuckling at his own joke.

While Jackson failed at fending off the man that was more than a foot taller than him, Madison was coming back from the bar. She had signed in and had a drink in each hand as she made her way back to her sibling, but seeing what was going on had her stop in her tracks. What she saw was her inexperienced sister standing rigid, eyes wide in fright as a large man held her close. “Hey you! Jolly Green Giant!” She called out as she marshed closer. “How about you keep your hands to yourself.”

Turning his head to the side Austin glared at the girl, not because of what she said, but because of the tone of her voice, it felt like she was talking down to him. He almost growled, it wouldn’t be the first time a girl he was going to hook up with had a friend that would cock block him. “How about you take your drinks and leave us alone, blondie here and I were just about to get to know one another and have some fun.”

Rolling her eyes Madison looked to her sister, raising an eyebrow. “Is that so? Jackie, do you want to go off and have fun with jolly green here?”

“My name is Austin, not jolly green.” Austin growled, pulling the girl who was flirting with him closer.

“N…” Jackson started to say when the man’s large hand pressed into his flesh on one side, forcing his hip to press into the man’s upper thigh. Fear started to grip Jackson, he never had been the rough and tumble type, but he was still a man and could never have expected himself to be in this sort of situation. He had to flirt and act like an air head at work in order to play his part, to not get found out and even his boss who knew he was a man still… Jackson felt himself shudder at the phantom taste of cum in his mouth and then Dunn’s words about not wanting it enough and then the worry about what that would mean for not just himself but others. Too afraid to say anything, Jackson did see the large man’s other hand form a fist. Swallowing hard, Jackson made eye contact with his sister and slowly shook his head, wanting to tell her to back off, that he would be okay. He was not going to let this man hurt her… and hopefully not himself either and was trying to work up the courage to tell Austin that it was okay, that the two of them could go get to know one another and leave Madison alone, but he didn’t get the chance.

“Oh, I’m truly sorry Austin, I didn’t mean to be rude and I’m sure you didn’t either, the problem we are having here is you want to get with my sister and my sister doesn’t want ANYTHINGGGGG to do with you. So what is going to happen is you are going to leave us alone, we are going to enjoy our drinks, watch the first round and then get in that pool there with the green jello. You, and please listen. You can go back to your seat and enjoy the show, or I can tell the bartender that two of the girls that were going to wrestle will be going home instead because of you. Do you think he will let us walk out the door? Or will he tell you that you need to walk out that door instead?”

Anger gripped the man, more than a few urges running through him, but he wasn’t so far in his cups that he didn’t understand where things would go. It felt incredibly unfair that the blonde would flirt with him, her friend then come over and not just cockblock him but threaten to have him kicked out and the blonde didn’t even stand up for him. “Teasing bitch.” He he spat before letting go of the pretty thing and stomping away.

Letting out a long breath, Jackson gazed at his sister. Her bitchy attitude saved him from having to spend time with the brute of a man and possibly saving him from doing something to keep him calm. He felt disgusted with himself that his conflict resolution skills had deteriorated to the point that he thought giving a blow job could resolve a situation. He was just about to hug her and maybe have a little cry when the large man’s words hit him. ‘Teasing bitch? I didn’t…’ Jackson wasn’t sure why he would say that and it hurt, he was a man… and yet… The thankfulness in his heart faded. ‘I’m a bitch… Madison used her bitchy powers to make him slink away and I was going to… if Madison hadn’t made me dress like, like…’ Taking the glass from his sister he gulped down the entire contents of the glass and regretting it right away. Downing a jack and coke was not like swallowing down a beer in a long pull at all.

Putting her hand on her siblings Madison looked at them worried. “You okay? You have to be careful with men like that. There is a reason some of us walk to our cars with our keys held in our hands like weapons.”

“I will be fine.” Jackson said after a few deep breaths, wishing he hadn’t just done that with his drink.

“Good, how about we get you another one of those and enjoy the first round of fights. I know I will enjoy ogling the first match and I’m sure if you record it your Linc will too.”

Touching two fingers to his temple Jackson closed his eyes for a second. “Maddy, please.”

“What!? He is a man, he will love it. Besides I’m sure he will enjoy watching the two of us roll around in the jello even more.”

“Maddy…”

“Yes?” Madison said with a bright teasing smile before taking a sip of her long island iced tea.

“I am sooo going to beat you up.” He said glaring at his older sister.

Jackson very much did enjoy watching the first match between two sexy ladies in the pool full of red jello as he enjoyed a second and then third drink. Not finding out till the third that the drinks were actually on the house for the four girls going to wrestle, and Maddy hasn’t paid a single cent. When it was his turn he felt good and buzzed and followed his sister’s lead when he saw her taking off her blouse and then shorts, the two of them getting down to their bikinis. Pulling his hair back into a ponytail Jackson raised his hand in the air as people cheered. With the **** in his system he only smiled a memory of some of his friends rowdily cheering for him after being on a mock stage for debate club. “You're going down, Maddy!” He declared as he stepped into the pool of jello. The cool semi solid gelatin felt odd on his feet, going between his toes.

Moving his feet slightly, Jackson wiggled his painted toes and shuffled his feet as he looked down, losing focus on what was going on around him. A small giggle escaped Jackson’s lips as he looked up at his sister who was rushing closer to him. His eyes opened wide as he braced himself for the impact, his drunken mind too distracted to have heard the bell for the match to start over the crowd and his own amusement with messing with the jello between his toes.

When his sister slammed into him Jackson almost fell out of the inflatable pool, but grabbing onto Maddy and shifting he feet he spun them both around the green jello sloshing about and flying in the air. Letting go of his sister at the end of the spin caused her to stumble back and trip over one of his feet. The trip hadn’t been intentional, he never was a fighter, but also never really imagined he would have so much trouble pushing Maddy around. “Down you go!” He yelled out.

Falling onto her back into the jello Madison didn’t feel the hard impact of the concrete underneath thanks to the inflatables spread out underneath. She went to kick up at Jackie and let out a growl as they not only didn’t get hit, but grabbed her leg in a way that caused her to only flail more as she tried to attack, get free and stand up all at the same time. In the end she was able to get two of the three, herself free and back to her feet thanks to the jello making her limb slippery. Taking one deep breath after another she charged once more, Madison had always been more comfortable on the attack than defending in her life and it didn’t matter if this was just some fun to blow off steam and boost her ego with the looks she knew they were getting, she wanted to win, Madison always wanted to win.

Jackson’s left foot slid backwards in the slippery substance, he could feel the stupid heavy fake tits sway and bounce pulling on his chest, the bikini top doing little to control them. It along with the tuft of hair that came free from his ponytail, it was all very distracting. Panting slightly from the effort his eyes caught the gaze of the large bar patron that had made him feel so **** less than an hour ago. His drunken mind lost focus on what he was doing as he paid attention to the hoots, hollers and comments of the men around him and his sister. That was when he felt Madison plow her shoulder into his stomach and flip him down into the jello, her falling down with him.

He wasn’t sure how it happened by somewhere in the thrashing about, the pool’s contents sloshing out to the bar, he ended up laying down across his sister, in her lap and his face buried down in the lime flavored gelatin. Jackson ended up swallowing a mouthful when he felt a hard slap to his only partially covered rear end, the bikini bottoms doing absolutely nothing to protect him from the slap. “AHH!” He yelled out as he pulled his head back, jello falling from his face. That was when he felt another and another slap to his rear end. ‘She is spanking me!’ he thought.

Bringing her hand down once more, Madison brought it down on the white flesh that looked like it hardly ever saw the light of the sun. “I think I win this one little sister.” She said as she slapped Jackie’s ass once more. “Admit it, tell me I won and that you will be a good little sister!”

“Get off me!” He yelled, trying to thrash, but she had one hand down on his back and his feet and hands couldn’t get any purchase in the slippery pool.

“Wrong answer. Who thinks I should teach my baby sister who is in charge!?” Madison yelled to the bar. With a roaring approval she continued her ****.

Smack, smack, smack

“Stop, stop!” Jackson cried, feeling like he was going to be sick, the drinks in his stomach threatening to come back up. “You win, you win! I will be a good girl!”

“Are you going to be a good baby sister and do as you are told?” Madison said loud enough for everyone to hear. She hadn’t planned to do this, but was feeling both buzzed and exhilarated. Thoughts of Jackie wanting to throw away this fantastic opportunity popped in her mind and she wasn’t going to let it fall away.

“Yes, I will be a good baby sister and do what you want!” Jackson whimpered, his body felt like it was covered in slime, it had even got into his bathing suit even as small as it was and could feel it in his ass crack even as his cheeks felt like they were on fire from the spanking.

Giving one more spank to Jackie’s ass, Madison raised both her fists into the air. “Are you not entertained!” She bellowed, quoting an old movie.