You go to Riley for your chastity problem

After a bit of debate in your head you decide to go with Riley. She seems a lot more chill then Ava. As well she doesn’t have anything against you unlike Ava. Who still probably believes it’s your fault that she got locked up in chastity. Besides that another point of friction between you, and Ava could be that you, and Harper sort of hooked up. You know that Ava, and Harper sort of have a dom sub relationship to some extent. And you get the feeling that Ava might be the jealous type. So if you came to her to help relive yourself, she might take the opportunity to just get **** on you instead. You shiver at the very thought, remembering how she can go all primal. Nope definitely nope, you are 100% better off with Riley.

Again looking around to make sure the teacher isn’t looking you quickly send Riley a text. You start out casual, going with a simple hi with a waving emoji. Waiting a minute you don’t get a response. You wait some more, two minutes no response. Then ten minutes, still nothing. You start to get a little antsy when finally your phone vibrates. Checking the screen you see it’s Riley. The text back is a simple hello with the same waving emoji you sent her. You breathe a sigh of relief, for a minute their you thought she wasn’t going to answer you back. Then how were you going to deal with your “little” problem?

“Hello Riley I don’t know if Amy told you but, she said I would be allowed to ask you guys for assistance if I needed help... well you know...” You text with a blushing emoji.

You almost feel a bit embarrassing asking Riley about helping you relive your balls. While Amy, Harper, and Ava had all been pretty over sexual towards you in one way or another, Riley had actually been a bit more reserved then all of the other’s. Of course she did tease you a bit when you got stripped naked, and when you were being froated with Ava. Yet she never really initiated anything sexual with you, or did anything sexual with you as far as you remembered. Of course you did sleep naked together, yet even then Riley didn’t make any moves on you. A bit of insecurity starts to creep into your mind as you think back. She didn’t think you were some how like gross or something did she? No you gotta be just over thinking things r-right? For a second you almost think about calling the whole thing off, yet then you feel your cock throb in your cage, and predictably this spurs you on to just ask regardless of any hang ups about it you have.

“You can say no if you want, but are free this afternoon for me to like come over to your place?” You text with a puppy dog eyed emoji, trying to make what your asking seem kind in a joking manner.

Sort of hoping that if you make your request seem not so serious it wouldn’t come off as so ****, and pathetic.
It seems you don’t need to be worried about that though as from the text back Riley seems more then happy to help.

“Sure Doug! No problem do you need a ride to pick you up as well? I don’t mind getting you.” Riley texts back.

“Yeah that would be great, and thanks for doing this.” You breath a sigh of relief as you text back with a praying emoji to show your gratitude to Riley.

“Hey don’t worry about it! And we can hang out too, after we get you all sorted out if you want!” Riley reply’s with a big smiling emoji.

“Sounds good!” You text back with a smiling emoji as well.

You then give Riley the time, and location to pick you up from, a before telling her goodbye, and getting back to focusing on school. Well as best you can focus with your whining cock... It only gets harder, and harder as the school day goes on though, both in the literal sense, and the metaphorical. As the last hour of school starts to tick down time feels like it starts to drag on. You feel yourself going more, and, more stir crazy as the minutes seem to get longer, and longer. By the last 10 minutes you can’t do anything but obsess over the time. Neglecting your school work, you eyes stay locked on your phone screen watching as the minutes count down.

Then finally the bell rings, and you practically sprint right out the door. Not even bothering to put your backpack over your shoulder you run with it in hand. Down the hallway behind you, you swear you can he a teacher screaming at you to stop running. You don’t even care though, you just want to get out of this school as soon as possible, and meet up with Riley. God how do your balls feel so full again, already it’s only been two days. Squeezing your eyes shut you keep running, busting out the front door you come to stop as you catch your breath a second.

“Oh hey Doug what’s up.” A familiar voice says from behind you.

Turning around you see Riley, leaning on the way next to the school’s front doors:

“Oh hah- hah h-hi Riley,” you say panting as you catch her your breath.

“Where’s the fire, your completely out of breath.” Riley chuckles, watching your wheeze, and suck in oxygen.

“S-sorry I just really wanted to, umm well you know...?” You say, the situation awkward for you to be able find the composer to be more descriptive.

God this feels so embarrassing, yet the feeling of embarrassment just makes you more horny. Damn Harper for unlocking your inner masochist! You just want Riley to pull your pants down, and roughly fondle your balls right here in the front of the school for everyone to see!!! W-well not really your pretty sure you would get both sent to jail for something like that but, the idea sure does turns you on.

“So then balls that backed up that bad eh?” Riley asks, interrupting your thoughts.

You nod, shifting in your stance as you play with the straps from your back pack. Dang now this really does feel, awkward. Not the fun sort of humiliating awkward that your inner masochist loves. That gross awkward that makes you feel uncomfortable enough to make you want to fade out of existence. With Harper things were direct, fast an linear. While a little scary at first, and a little humiliating it wasn’t this awkward. Right now you just feel like a burden. Like your asking your friend to help you out with some sort weird medical condition.

“S-sorry about this you know it’s just it was down to you and Ava, and I thought you were the better choice for now.” You say, your voice trembling slightly as your gaze meets Riley’s friendly smiling expression.

“Hehe honestly that’s probably for the best, Ava kindaaaa heard about your little meet up with Harper, and she’s kindaaaa fuming about it” Riley chuckles, with her smile shifting from friendly to amused.

“W-woah, r-really I didn’t mean to make her that mad I didn’t even really think about that when I contacted Harper.” You say a bead of sweat rolling down as you remember how deceptively strong Ava is.

“Ehh don’t worry about it, she can be a bit emotional at times though she’s not dangerous least she would do would throw a tantrum at you, as well she doesn’t really hold grudges for very long so she’ll probably forget it by the end of the week.” Riley says, like she’s experienced this sort of thing with Ava before.

Again Ava really does seem to be just the bratty child of the group that everyone puts up or punishes, when she gets to rody.

“Well I guess it’s a relief I haven’t made a permanent enemy out of her.” You smile at Riley, as you joke.

“Haha that’s for sure, now let’s get a move, you wanted your balls drained didn’t you.” Riley says motioning for you to follow.

A shiver of desire shoots down your spine, and your cock throbs as you hear that. Hell yeah draining sounds so good! Quickly you step after Riley as she leads you to her car.
Climbing into the passenger side of her red convertible, the strawberry blonde looks so pretty right now. Maybe it’s because your so horny right now, or maybe it’s the way the sun light is hitting her, but Riley for some reason looks so beautiful right. She sees you starting, and gives you a cheerful smile, a bit of her subtle pink lip gloss shimmering light from the reflection of the sun.

“You got a face like one of those fan boys I see at our concerts right now Doug.” Riley giggles in a soft playful tone.

“Sorry you just a really nice outfit.” Doug lies, him not even really taking notice of Riley’s clothes since she showed up.

“Oh really what do you like about it?” Riley asks examining her own outfit, as she looks to see what might have caught your eye.

“I-I..umm.,,”

Quickly you look over Riley’s state of dress trying to find something to mention so she doesn’t think you were just making up a lame excuse. Which you were... First thing you see is the bright blue bandana, she has tied around her head like a head back. You wonder exactly how out of it you actually are if, you weren’t able to notice that when you where looking at her hair. Damn this chastity cage really does a number on your head! Next is the reflective pair of aviation sunglasses which obscures her sky blue eyes. Then you look down to her top, the good bit of cleavage from her plain white t-shirt immediately catches your eyes. Riley’s soft looking boobs make your dick twitch, sending a bit of a sting down your dick as any movement squishes you hard against your plastic pink captor. Tearing your eyes away from her boobs you notice the nice jean jacket she is wearing. It’s crisp, clean, and a nice light blue color, with a few silver buttons, and pockets on the front. As well they actually seems to be some cloth on the inside which makes the jacket look actually rather comfy. Her pants as some skinny blue jeans that match the jacket, with a few purposely placed rips on the pant legs. For shoes, Riley has on what look like skate shoes, or at least a brand that you’ve seen the local skate rats at school where a couple of times.

“I like your jacket it looks very trendy.” You say trying to sound as confident, and natural as you can as you speak.

“Yeah I know right I thought it looked good when I saw it the store, nice to know I haven’t lost my taste in fashion.” Riley says flashing her teeth with a cheerful grin.

“And yes if your wondering I’m the quote on quote, normie of the band, if you couldn’t already tell.” Riley chuckles as she puts the key into the ignition.

“Oh so are you...”

“I’m not a poser if that’s what your thinking, I’m still into the whole metal scene, yet I have some more main stream interests then the other girls.” Riley says a bit tickled as she remembers her interests being more then once playfully scrutinized by the other band members.

She laughs thinking of the time Amy once made fun of her when she found out Riley was into trashy tv office dramas. After which Amy then tripped over an Amp, and face planted directly into the floor.

“Yeah, so tell me Doug how has it been hanging out with us so far?” Riley asks, making some idle conversation as she starts pulling out of the school lot.

“It’s been a bit intense.... some times, but you guys all seem to be really cool, I really don’t mind hanging out with you at all.” You respond remembering not just the sex, but the fun you had just sort of hanging out eating pizza, watching a movies, and playing games.

“Aw that’s really sweet of you to say Doug honestly I hope you can keep hanging out with the rest or the band members, they don’t seem to hang out with many boys that aren’t just groupies.” Riley’s says, a hint of concern in her voice.

She then sighs.

“Really I’m kinda glad for it, I was kinda worried about the girls sort of changing...” Riley pauses, leaving the subject there unless you pressed the conversation.

Which you do.

“What do you mean?”

Riley furrows her brow, feeling a bit hesitant to actually speak her thoughts now you’ve actually asked. She shakes it off, deciding it’s better to get it out in the open, rather then let your curiosity and, imagination run wild in the silence.

“Well first just let me say I don’t try to act like I’m better then any one else, or that I am the moral consensus of the band or anything, but we kinda got really popular recently like about half a year ago.” Riley explains, seeming a bit skeptical of the idea of the band getting big.

“And because of that as you can imagine we had quiet a lot of boys, and even some times girls throwing themselves at us, especially at live shows.”

You nod as Riley glance over to you momentarily from the road, checking that your actually listening.

“Now I’m not like some Puritan, I’ve had my fair share of fun with fans to, I mean who wouldn’t, there’s nothing really wrong with it in principle, and a lot of our fans are actually pretty hot.”

Riley then grins reminiscing about some of the hot sex she, and the girls had after the concerts they’ve had, before her expression turns serious again.

“ahem Still I seem to have a lower labito then the the other girls though I’m not saying I don’t have the same vices... it’s just that it’s not as big as a problem from me to... gah I’m sounding so conceded, and holier then thou right now.” Riley mumbles, aggravated with herself that she can’t make the words come out right.

You stay quiet, waiting patiently as Riley tries to gather her thoughts. She seems to be having some trouble articulating what she wants to say in a way that doesn’t make it sound like she’s bad mouthing the other girls. Then after a few seconds of silence, with Riley mulling over the right words in her head she again speak.

“Sorry what I’m trying to say is you know how there are a bunch of famous bands that it like always comes out that actually they were doing really messed up stuff to their groupies, you know like **** or stuff with out their consent even to some under free fans.” Riley pauses for a second looking your response.

“Yeah.” You nod thinking you heard something along those lines at some point.

“Well, while all the girls in the band are good people I know fame can corrupt, and change good people, and I was kinda worried before that we were changing, for the worse you know...” Riley says, pushing her sunglasses up on her nose.

“You guys seemed fine to me at the sleep over, I... wasn’t really against any of the things we did, like I didn’t get the sense that you weren’t going to make do something I won’t on some level agree to.”

“Even the chastity cage.” Riley asks raising an eyebrow.

“Even the chastity cage, and I’m sure that if told Amy that I genuinely wanted or needed out she would let me go, you guys really don’t seem like bad people to me Riley...” You say with a small reassuring smile on your face.

“I’m glad to hear that Doug, that gives me a bit of peace of mind.” Riley speak in a soft grateful tone.

She pauses for minute then grins as she looks over to you for a second.

“Anywayyysss on a less serious note I heard you had a bit of an awakening with Harper.” Riley teases, no doubt referring to your masochist side being revealed.

You feel your face start to go red, as Riley mentions that. You wonder just how much Harper has told the other girls of yesterday, because at this point it seems to be just common knowledge what went on at her house. Though you can’t say you mind them knowing. Talking about it, teasing you about. The idea of them getting together, and swapping stories about their experiences with you, it really turns you on. It makes you feel like your something special to the girls, a sexy little topic shared between all the band members. You squirm in your seat as you feel yourself start to throb. God you can’t wait till you finally reach your destination, you really want to cum.

“So tell me how did it happen, was it something sort of clicked, or was more so the pain gradually started to feel good?” Riley chuckles, though you can tell their genuine curiosity behind the laughter.

“Uhhh maybe a little of both, it’s honestly kind of hard to describe what I was feeling at the time, it was a real in the moment thing.”

“Hmmm sounds like an almost religious experience, also I heard from Harper you and her really hit it off during your get together, that true?”

“Yeah Harper is actually really nice you know I thought she would be a bit could especially after she uhh, you know whipped me, yet she was actually really considerate to me the whole time I had a session with her.

“Yeah she’s a big old softy once you get to know her”.

“And well I was also kinda surprised that she wasn’t planning on you know... using me to get herself off.”

“Not surprise Harper is big on boundaries, and rules, she wouldn’t do something that she didn’t have your consent for before head, which her getting of with your body doesn’t seem to be something she had, well at least at first she didn’t.” Riley says with a knowing look on her face.

“S-so she told you about that?” You say remembering how you had volunteered to pay Harper back after made you cum.

“How you give her a world class buttjob yeah she did!”

You feel yourself blushing even harder now,

“That was nice of you I sure Harper really appreciates that, and not in just a dom way, but in a friend way as well.”

“I don’t think anyone can take what we did in a friend way hehe.” You says laughing a little.

“Friends with benefits they could, besides isn’t looking out for each other’s needs what friends are supposed to do?” Riley says, pleaded by her on cleaver logic.

“I guess.” You say, nodding with an grin.

Then Riley pulls the car into a small parking lot next to a large sky scraper. Looking around you realize she’s driven you all the way out to the city.

“You live in there?” You ask craning your neck up to see the top of the building.

“Yup, I live almost all the way at the top but before we go in do you want to try something a little funnnn?”

She then hits a button on the dashboard of her car, and the roof of her convertible goes up giving the two of you a bit of privacy. She then reaches into the back seat, and grabs a dog collar, and leash.

“So Harper told me how she made you walk up to her house naked, and I was wondering if you would like to repeat that little scene with this leash, I hear masochist love a bit of humiliation.” Riley grins at you.

“In-in there?!?!” You say mouth agape as you point to the large glass building.

Riley nods.

“We’ll be arrested!!!”

Surely there are people in that building that wouldn’t be found of you walking in there naked, Riley can’t really be serious with this can she?!?!

“Nah they aren’t gonna make criminal out of me or anyone bring with me, I pay too well, besides I’ve seen stuff like this before go on in there before, and the front desk never cared, I think they have at least a few kinky residents living their so they might have gotten used to some more extroverted activities.”Riley says spinning the dog collar around her finger.

“It’s really up to you though I’m not commanding you to do it or anything like that, I’m just trying to pander a little to what I think are your preferences.” Riley shrugs, leaning back in her chair as she awaits an answer.

You look over to the building again, while the thought of that scenario does make your dick press hard agains your cage, your not sure if your ready for something this intense. Before, when you did something like this with Harper it was just her house in a small rural area, and the only one who saw you was her neighbor, who had seen Harper have subs with her before. Yet this is a public building in the city, if you go in there it’s practically a guaranty that your going to be seen. And by complete strangers no less, they will see you naked locked in chastity, a dog leash around your neck, with not even a stitch of clothing on. What will they say, what will think? Will they judge you, will they think your a slut?

Holy fuck, the idea of that it sounds so shameful, yet it also turns you on so much. You feel yourself leaking just thinking about it. Yet are you truly ready for something so intense? Can you really handle it?