Disable your Ad Blocker! Thanks :)
Chapter 26
by
lolhappy250
So where are you now?
Local rec centre
Considering how much Caitlin gushed about her workplace while trying to **** you to join her, you weren’t expecting this. In your mind you didn’t seen a dedicated gym losing in quality to something squeezed together with a half dozen or so other facilities.
Regardless of what you expected, you were so glad to be able to get out of the car with your mother that you flung yourself from your seat the first chance you got and stretched with satisfaction.
“Jesus, you guys are sweating bullets already.” Caitlin laughed as she stepped out of your mother’s car and looked you over.
“Oh… yeah, my AC crapped out on me the other day.”
“I was wondering why you didn’t turn it on.” Your mother added with a nervous chuckle.
Your mother wasn’t even half the liar you or your siblings were, but Caitlin had no way of knowing just what kind of conversation you had just had, so thankfully she bought it your story with a smirk towards your crap-mobile.
You brought that on yourself so you did your best to brush it off and let your sister lead the way towards the rather large building. Once inside you started to get a decent idea why she liked this place so much though. The outside was pretty plain and simple, but the inside was chic and modern, it used mostly muted colours, like shades of gray with a bit of brown where it could get away with. It also became apparent very quickly that despite the size of the building it must’ve only had two floors, because the lobby ceiling must’ve been fifteen feet up at least.
You were pretty quickly lead through the packed lobby past the receptionist. Along the way you saw some windows leading into a pretty massive indoor pool. As you wove through the crowd you also noticed quite a handful of glances aimed towards your group, upon closer inspection they were specifically aimed towards Nalini. Perhaps influenced by your wallet, few gazes had any real emotion to them, more like they were just acknowledging that she was kind of out of place, although a few male gazes definitely showed appreciation. Regardless of what you saw in the looks, Nalini couldn’t hide her own embarrassment entirely. The busty half naked bank manager had a stiff expression on her red face and made it a point to not look at anyone while she stuck close to Caitlin who was leading the charge.
Before long you found yourself climbing a huge staircase. Immediately upon making it to the second floor the loud buzz of the first floor dimmed to near complete silence, and you were left with a cozy hum inside a carpeted hallway. There wasn’t anyone in sight here.
When Caitlin led you through a doorway helpfully labeled “gym,” you found that you were in another, much smaller, reception area, and the only person in sight was a thin, raven haired woman in glasses behind a small half circle desk.
“Hey Tina!” Your sister called out.
“Caitlin! And Erin! And some new faces huh? That’s always good!” Tina smiled at your sister and mother, then the rest of you in turn, taking an extra long glance at Nalini’s barely covered lower half, but making no particular note of it.
Caitlin then gestured to Nalini and Emma,
“You mind if I give them a trial run today?”
“Not at all, go ahead in.” She gestured helpfully towards the door to her side, but then her smile faltered just a hair and she looked at you.
As much as you wanted to roll your eyes you knew your sister would do this to you, a single day pass was probably chump change, even for you, so it would’ve been a no brainer that she’d try to get you to pay it.
“Actually, how long would it take to get a membership?” You cleared your throat and approached the counter.
“Oh my god! Are you serious?” Caitlin for once in her life looked genuinely shocked and giddy at something you had said.
“Hey I’m just getting a membership, don’t get your titties in a twist.” Like the good younger brother you were though, you tried to throw cold water on her good mood.
“It should only take about five minutes, give or take a few.” Tina replied.
“Hey, make sure to give him the friends and family discount.” Caitlin excitedly squeal at Tina, but then looked at you with a snooty sneer, “The one that makes it cheaper.”
“Look, I get that I could do with some more exercise, but right now I can’t afford to pay my own sister to yell at me while I work out, especially since I already get that for free when I’m at home.”
Caitlin started to pout, but Tina piped up before she could say anything,
“Actually, we offer discounted rates if you bundle your membership with a personal trainer and if this is your first time signing up for our gym facilities we give you your first year with a personal trainer another slash in prices.” Tina went about tapping at her computer leaving you to think about it.
Well that was all well and good, but you’d still be paying your sister for something you weren’t even sure you wanted.
“In fact, if this is your first time it looks like you’ll be getting the best deal, by far, by bundling everything together.”
“See! You should have more faith in your big sister! I’ll take good care of you.” Caitlin spread her arms wide and gave you a cheeky smirk.
“Plus it’ll be entirely up to you if you want to use her or not” Tina added with a smile.
Before you could stop yourself you started looking Caitlin up and down – Wait! Damn straight it’ll be up to you! Despite all the evidence to the contrary, you weren’t a sick pervert.
“Yeah, I guess that sounds fine, as long as I don’t have to use her.” You tried to shake the perverse thoughts from your head and asked for a membership form.
Caitlin looked ready to argue with you, but before she could make more than a disgruntled harrumph, a sly grin spread across her face. You really didn’t like the look of that. Before you could say anything to her though she ushered everyone else through the doorway to the side and left you alone with Tina.
While you waited for her to get your forms together you did your best to slyly check her out. You expected someone who worked at a gym to be jacked, but if she used the facilities herself it wasn’t quite that obvious. She looked like a thin, wisp of a thing, and her narrow half rimmed glasses only helped project her fragile appearance. When she got up to grab your paperwork out of a printer you couldn’t help but admire her statuesque form. Even if she lacked considerably muscle mass or tone, she was a striking figure. Her ass was small but it was hard to deny results there, she clearly did something in the gym, but her best features had to be her long, silky legs sticking out of her mini skirt.
You’d have to fuck her before you leave today.
“Here you go. It should be pretty straight forward stuff, but if you have any questions feel free to ask.”
You simply smiled and thanked the woman, and made no move to hide the readjustment of your pants. She made no reaction to that however, seemingly unconcerned with your sordid thoughts about her. You didn’t doubt she had experience with complete strangers undressing her with their eyes, but she had no idea how much further you were planning on going.
After finishing up the paperwork and saying your farewells to more money than your were expecting to be spending today, you shuffled off to find the rest of your party.
The gym was actually far more impressive than you were expecting, you could only name maybe half the equipment, the rest you’d only seen on T.V and in the background of random girl’s instagram selfies.
Even if the setup was impressive, apparently Caitlin wasn’t kidding about having a slow day, there were only a dozen or so people scattered about, most off by themselves and pretty much all of them looked like seasoned gym veterans that wouldn’t need her help, so it wasn’t hard to find your group. For one, Caitlin was waving you over, secondly. it was the largest group in the gym with four people, and thirdly, the second largest group, two sweaty ‘dude-bro’ looking guys sitting on a bench, were quite obviously ogling them all.
When you approached the ladies they were in the middle of stretching.
“Alright you three, turn around and do some toe touches.” Caitlin barked far more seriously than she usually presented herself, “And you!” She whipped around violently and stuck a finger in your face, catching you off guard, “Drop your pants.”
“Say what?” You squinted down her finger at her face.
She looked dead serious for some reason.
“Don’t make me wrestle them off you.” She flexed her arms intimidatingly.
Even if her arms weren’t all that big, they looked like they were carved from marble. If she legitimately wanted your pants off there probably wasn’t much you could do to resist that didn’t involve punching or biting your own sister. That said, even if you didn’t know what game she was playing you seriously doubted –
In one swift motion your sister squatted down and pulled your sweatpants and underwear to your ankles.
“Well shit! Someone’s already raring to go!” Caitlin gave a wide eyed smile to your cock, bobbing inches from her face.
“Caitlin? What are you doing?” Your mother innocently asked from between her knees before standing up, putting her hands on her shapely hips and cocking an eyebrow at your sister.
You were already starting to get used to using magic as an explanation for this weird shit, but still couldn't shake the instinctual reaction to look around to make sure no one was pulling out their phones.
Of course no one was the least bit interested, even the dude-bros from before seemed to be focused on their own exercise now that you had your dick out.
“Ugh, mom! Just turn around and grab your ankles.” Caitlin scoffed and stood up straight.
“Huh?”
Yeah, huh?
“I’m trying to do my job here, and that requires everyone to do their part.” She fluttered her fingers at your mother, gesturing for her to turn around.
“And that requires you to… expose your brother?” Your mother didn’t budge, but she did look down at your meat for a moment before snapping her attention back up, meeting your eyes and going red in the face.
“That’s why I did it.” Caitlin rolled her eyes and sighed, “So turn around and start doing toe touches please, while I take special care of a tricky client.”
After a moment’s pause, and seemingly unable to find an argument, your mother sighed and did as your sister commanded.
Admittedly you’d never been to a gym before, but this right here… this… this was kind of –
Just then Caitlin grabbed your dick.
“Hey! Whoa! That’s my special area, what the hell!” You immediately tried to take a step back, but with your pants around your ankles you had to abort that to avoid tripping and found yourself stuck with your dick in your sister’s hand.
“I kind of figured. That’s why I grabbed it.”
“Well could you not?” You reached for her wrist, determined not to give in to this perversion.
Right now you were the only sane person here, unaffected by your wallet, it was your responsibility to not fuck your sister.
“Oh come on! You’re telling me you’re not hard because of that?” Caitlin intercepted your hand, got to her feet, and in one swift motion twisted your arm behind your back, then with her free hand grabbed your chin and **** you to look towards the line up of Nalini, Emma and your mother, their legs spread shoulder width apart, and bent over touching their toes.
Emma was unfortunately wearing something loose and not very revealing, but your mother’s pants seemed to be straining to hold together when viewed from this angle, and Nalini’s thong was having obvious trouble covering anything.
Before you could articulate a response that wasn’t a pained gasp from how you were being manhandled, Caitlin reached back down, and pumped her hand up the length of your meat while whispering into your ear,
“I have you for the next hour, so how about we make this fun?”
“I already said I’m not using you, you thirsty ho.” You grunted through the pain of your pinned arm and regrettable amount of pleasure at your own flesh and blood relative stroking your meat.
“Just for that you’re not allowed to cum for the next hour either.” Caitlin finally released you and shoved you forward, giving you a massive shit eating grin as you turned to face her, “You didn’t want me shouting at you so you get this for motivation instead. Now out of those pants and get to stretching too.”
Okay… so apparently you brought this on yourself? Great….
It went without saying that you pulled your pants back up. You’d already gone farther with family today than you felt comfortable with. Regardless of how painfully hard you were, you still had principles.
Thankfully Caitlin left you alone with only a slight frown.
All that said, while she was here helping newbies get used to the gym you didn’t see why you couldn’t join in. Only hiccup being the stretches she gave you coincidentally involved you standing in place, and staring down at the asses of the other three. And she made certain that none of the girls got out of line,
“Could you face that way please?” Caitlin tapped her foot and pointed Nalini in the direction the other two were facing.
Nalini seemed a little confused at the correction, but nonetheless crawled away from you and showed off her tan rear end, sandwiching a string that made up the back end of her thong.
“Okay, now extend your leg out slowly, try to keep it from shaking.” Despite the position she put Nalini in, Caitlin seemed to be giving genuine advice and finally acting professional, “You should feel your glutes flexing right here, right?” She wasted no time grabbing hold of one of Nalini’s buttcheeks and started groping it, all while smiling back at you.
“Yeah, I think I got it.” Nalini choked out in clear surprise.
You couldn’t see her face from your angle, but you got the distinct feeling she was a little weirded out by being groped by her personal trainer.
Caitlin was unperturbed by Nalini’s hesitance though and moved on to helping her guide her leg out in a circle,
“Your leg should go out about this far before you bring it in, alright?” Caitlin kept her hand on Nalini’s ass, spreading her cheek and used her other hand to hold her leg out by the ankle, then she looked back at you with a wink and a lick of her lips, “This looks good from where you are, right, John?”
You wanted nothing more to quip something back to her, but Nalini’s head whipped around and she let out a gasp,
“Oh! I think I got it!”
Just what did she get you had to wonder?
Either way, your sister seemed done giving you an eyeful of Nalini’s ass for now, and went on to help Emma and your mother with actual, genuine professionalism. Oh who are you kidding? Neither of them were stripped down to a thong, but your sister still pawed at their asses for you.
“Ah! Caitlin!” Your mother squeaked in shock when your sister first slapped her butt, but was quickly shot down by having her form ridiculed and thus your older sister had free reign over your mother's ass.
Emma on the other hand not so subtly pretended to not know what your sister was getting at and got a good long ass groping out of it.
You could only thank your lucky stars when you were moved to some exercise you were familiar with, bench presses.
“Okay, you can spot Emma, hopefully you’re at least stronger than her.”
You rolled your eyes at that, your raging hardon took most of your sarcastic faculties at the moment, but hopefully some actual exercise would redirect some blood and help fix that.
After bouncing off for a moment to get Nalini and your mother set up, Caitlin came back to watch you spot Emma,
“Just remember, you’re not trying to take the barbell from her, just take on some of the weight for her once you see her struggling, she’s still the one in charge.”
“I got it.” You rested your hands on the bar and let Emma work it up and down.
One, two, three, your pants were suddenly down, five…,
“Dammit woman!” You immediately turned on her and reached for your pants.
“Watch the barbell!” Caitlin intercepted you in an intimidating rage, forcing you to stand back up straight, abandon your pants, and face Emma again “Gym safety is important! You’re not allowed to be distracted by pointless bullshit while you’re supposed to be looking out for your fellow gym goers!” She kept up her stern tone, but there was the hint of a grin on her face that cheesed you off.
Pointless bullshit! Your pants were around your ankles! Her logic was fucked up, but thanks to your wallets effects it was sound, so all you could do was keep an eye out for Emma while your raging hard on bobbed right over her face.
As it turned out Emma didn’t have much more in her, so you jumped in and helped her put the barbell back into place, quite expertly if you were to say so yourself. Of course Caitlin wasn’t done with you quite yet.
“Alright, you’ve got thirty seconds to rest and then we’ll try for another set.” With that, she reached around your back, grabbing your side and while squeezing her hot form against you, wrapped her slender fingers around your shaft and ran up the length of it slowly, counting off the seconds with every pump.
Your sister had always just been just that, family, blood, someone you absolutely never wanted to fuck, and while you’d never been scared of her, she was always an intimidating woman. She was the only one in your family that matched your height and had a body that could’ve been carved from stone. Right now though you were seeing her in a vastly different light.
You always evaluated her as your physical equal at worst, and frankly speaking, your superior pretty much every other time, but with her body pressed up against you, you couldn’t say that quite as confidently anymore. Sure, you didn’t doubt she could kick your ass in any physical activity, hell, even if it was by surprise, she got the best of you a few minutes ago, but with her form squeezed up against you, you noticed that even if she was just as tall as you, she wasn’t nearly as broad shouldered, even her arms, toned as they were, weren’t really any bigger than yours. Seeing, and feeling her surprisingly slender and dainty fingers barely able to wrap around your meat and working their way up its length over Emma’s exhausted and red face, only further drove home that you were bigger than your ‘big sister,’ that was simply a fact.
For all her muscles, despite her blood relation to you, she was still just a woman, plain and simple.… and since you paid her… if you really wanted….
With a grunt of dismay you **** the thought from your head and shoved your sister away,
“Let go of my weiner, woman!” You were hard as stone at her touch and the only hope you had at calming down was to try and distance yourself from her.
It was getting tough to convince yourself resistance was the right thing to do though.
“You don’t like my handjob?” Caitlin put on an exaggerated pout.
“Your my sister! Of course not!”
Both Caitlin and Emma gave a pointed look to your twitching member. Granted one didn’t have much of a choice, but their point was still obvious.
“Well is that so…” Caitlin walked behind you with a smirk.
You tried turning to face her, but a hard shove, which you felt was in retaliation for your own ****, had you stumble forward and slap your dick down on Emma’s face.
“...I suppose you want something better than, huh?” Caitlin growled in your ear from behind, sending a shiver down your spine.
Your dick twitched in response to her hot, breathy voice in your ear, giving Emma another tap on the nose.
“Should I be helping….” Emma mumbled, her hot breath only further tickling your cock.
“Just get back to your set, I’ll take care of him!” Still behind you, Caitlin reached over and juggled your balls, lifting your cock form Emma’s face as she did.
Just as you started to protest once more, her grip tightened and you started to see stars,
“Eyes forward and hands on the barbell!”
“You fucking bitch!”
“Haha! Yeah, how about that!” Mercifully Caitlin relaxed her grip, although she didn’t release your balls from her surprisingly small, clammy hand.
You felt like your legs were going to give out and that you were going to puke, but with your kryptonite in her hands, all you could do was follow your sisters simple orders.
You always knew your older sister as a boisterous, boundary stomping personality. Now that literally grabbing her brother by the balls had no taboo you should’ve known that she wouldn’t have hesitated to do just that to fit whatever agenda she had. It was still despicable of her as far as you were concerned.
You did your best to focus on Emma, despite your precarious predicament and the pain radiating through your body, but of course, Caitlin wasn’t content with just cradling your jewels,
“So if my handjob’s aren’t good enough what do you want from me?” She giggled teasingly into your ear, “You want your big sis to **** on your cock? Maybe you want me to ride your dick?”
“How about I rip you a new asshole?” You were still sore over your eggs being crushed just so she could make a point.
“Now we’re getting somewhere!” Caitlin finally released your balls and embraced you in a hug from behind, placing both her hands on your meat, “But you can’t expect me to believe that’s as kinky as you get.”
“Ex-fucking-cuse me? You nearly crushed my balls so I’d tell you my fetishes?”
“Eyes forward!” Caitlin barked, scaring you back in line, then added in a passive tone, “Yeah, pretty much.”
You were stupefied for a moment, then in a blind rage shouted back at her,
“Well how about you let me knock you the fuck up then? I’d love that! See how much fun we can have pushing a football out of your cunt!”
“Now there’s an idea….” Caitlin snickered at your perverted taunt.
She seemed completely unperturbed, but in your rage you didn’t see that as genuine.
Just then Caitlin released you from her embrace and ordered you to switch with Emma. Before doing so, in a weak attempt at protest, you pulled your pants back up then took the bench.
Just as you predicted though, your pants only stayed on until you lifted the bar, after which they were yanked off and tossed aside.
“Jesus, woman!” Even if you were expecting it, you weren’t prepared for just how rough your sister was being and nearly lost control of the barbell if not for Emma’s help.
“Oh calm down. I’m just helping you get comfortable.” Caitlin gave a sultry chuckle and straddled your naked waist.
The only thing separating your iron hard cock from your sisters cunt at this point was her bike shorts and you hoped some panties, but your throbbing meat was having a bit of difficulty feeling anything other than the incredible heat coming from between your sister’s legs.
“Get comfortable my ass! You’re practically fucking me!”
“Oh you wish.” Caitlin chuckled and leaned over you, making extra sure to slide her thinly covered cunt over your meat, “But tell you what…” she leaned in to your ear, so close her hot breath sent a shiver down your spine.
It took everything you had not to let the barbell drop on both your heads right there.
“If you work hard enough and by the end of your membership manage to make me your bitch, I’ll let you do whatever you want to me.”
“What?” You shouted up at her, as your arms started to give out and refused to lift the barbell more than halfway back up.
“You heard me!” Caitlin sat back up with a fit of condescending giggles as Emma came to your rescue, just barely, “Before I’m done being your personal trainer, if you can push me down and fuck me stupid I’ll be your personal whatever. How’s that for motivation? Fuck my ass, knock me up, keep me as a pet like Nalini, you name it.”
“Well I can’t speak about this method of motivation in particular…” Your mother walked up with Nalini, both apparently done with their sets, “...But I’m sure you’ll be pushing her down and going to town in no time. She’s really very good.”
Regardless of how you felt about your mother encouraging you to accept your sisters slutty offer, your cock definitely liked it, twitching underneath Caitlin hard enough to make her squirm and look down.
“You think I want to see you every day?” You tried to sit up, but before you got even halfway Caitlin slammed you back down with ease using only a single hand knocking, the air from your lungs.
“Not so fast there big boy. You’ve still got two more sets left.”
The more she pushed you around like a child the less you felt regret at the thought of violating her. Even now, you had a hard time reprimanding yourself for the mere thought of knocking her on her ass and **** her with your cock to wipe that smirk from her face.
“In fact, how about this? If you cum before you’re finished the deal’s off.” Caitlin started to rock her hips, grinding her thinly covered cunt up and down the length of your shaft.
“And you know, not that I’m saying you should do this to your own sister, but if you wanted, you could just gag her and tie her up when you’re not having sex with her, right?” Your mother not so helpfully tried to assuage your doubts.
Do you cum?
Disable your Ad Blocker! Thanks :)
Sexual Privilege
Freeuse for One
These branching stories are going to have 3 very simple premises: 1) You exist in a world where your character AND ONLY your character gets to have sex with whatever group or groups of people you choose wherever and whenever he or she desires. 2) The circumstances under which he or she can have sex with that group can be specified generally or specifically. 3) The response of the people you have sex with and/or the general public can be chosen.
Updated on Jun 20, 2026
by Cross C
Created on Aug 31, 2017
by SanctifiedVillified
You can customize this story. Simply enter the following details about the main characters.
With every decision at the end of a chapter your game state can change. Here are your current variables.
- 216,863 Likes
- 45,403,977 Views
- 8,566 Favorites
- 49,775 Bookmarks
- 4,255 Chapters
- 57 Chapters Deep
Comments moved below the chapter.
Jump to comments
Comments