"I was thinking you could play with my butt, then let me out?"

As Rose danced out of the room with your mom's dildo, the nauseous feeling in your stomach kind of went away. Too late to worry about what the guys might say, and only a bit of time to worry about what to pick out from your mom's stash of toys to guarantee Rose let you out of your cage. She definitely had her eye on your mom's strap-on harnesses, and her plug collection, when you were showing them to her, so you figured a little exploratory butt play might be on the table... Your mom had certainly prepared you well for such a thing, but you'd never really had anything beyond a plug and her fingers inside you when she needed to "milk you" for treatment on those days when you hadn't earned enough points through the week to get your cage off... No doubt you cum every time your mom works your prostate over, but maybe with Rose you could actually enjoy it instead of trying to hide how it always made you feel. Kind of invigorated by the thought, and grabbing a nice looking butt plug and a slim vibrator from your mom's case, it was time to start getting ready.

Dropping your shorts and panties to the floor while you walked into your mom's bathroom, you lifted your leg up onto the counter and checked your crack to see if there was anything you needed to clean up before getting ready. You always washed well, per your mom's standing orders, and used the douche she had installed in your shower with every bath, but you had to be sure. No reason letting Rose think you were gross, on top of everything else she had seen today! Everything looked clean and smooth, as far as you could tell, so you lubed up a finger and tested your hole. The coolness of the lube sent a shiver up your spine as your finger slid in with no issue. The lack of resistance was clearly a sign that your mom had trained you well, and after just a few more applications of lube with your fingers, it was time to loosen up deeper with the vibrator. Your mom had a stash of training dildos, but they were stored away in your bathroom, so one of her vibrators was the best option you had. It was just about 5 inches long and purple, no ridges or defining features, so it was a perfect fit. Stroking it in and out of your ass carefully, not wanting to lose it inside yourself, for a few moments had your dick straining in its cage... More and more confident that you were going to enjoy the night, you closed your eyes and nearly made yourself cum just by imagining Rose behind you, fucking you! With a startled gasp and a dribble of cum dangling from your cage, you needed to hurry up, so you cast the vibrator aside and aimed the decently sized plug at your back door. Leg on the counter, it took a bit of effort and more lube, but with a satisfying *pop* the plug was inside your ass.

"Holy shit... my ass actually looks kinda good with this thing in it? What the hell... I can't believe this is happening..."

Kind of at a loss for words on how you really felt, and pondering if you more than liked how it felt to willingly slip a plug in your ass, you walked out of the bathroom after wiping away the excess lube from your butt cheeks, carrying the bottle of it for Rose to use on whichever toy she decided to hook into the strap-on harness. You moved everything off the bed except for the things you picked out before remembering that you were naked from the waist down, so you rushed to your mom's drawer and pulled out a fresh pair of panties. A lacy, blue pair of cheeky bottoms that fit you surprisingly well, then you had everything neatly arranged, you just couldn't stop feeling your butt and the plug so snugly stuffing it. The panties fit surprisingly well. You pulled at the jeweled end of the plug idly as you stroked your backside and let it slide slowly out, bit by bit, until your hole was just about to release it, then let it go; your ass greedily sucking it back in. A small, wet dot appeared on the front of your panties, but you kept pulling and releasing, mesmerized at how it always just pulled itself right back in.

Your playtime was interrupted at last when you heard Rose lock your mom's door behind her. Gasping, and twirling around turning to face her while covering yourself she was looking equally curious and bemused. "Um... babe, you're not getting a little too carried away in here without me, are you? You looked so... distracted... with that big ol' plug in your butt just now... Can you show me how big it is?"

Rose motioned for you to turn your back to her again, and lean down over the bed, like you were when she walked in. Not seeing a reason to fight her request, you spun to put your back to her and started to massage the base of the plug with your fingers through your panties; sending a shudder down your spine. Kipping a leg up on the bed, you spread your cheeks apart to let her see the jeweled base, prompting an, "Ooh fancy!" from Rose. Her hand slapped your ass in approval and she started squeezing your cheeks; remarking on how soft and smooth you felt in your mom's panties.

"God Chris, this ass is like... actually nice! So round and soft... like really soft! And you look so tasty in these panties too. I think they suit you really well... Such a pretty little butt... Honestly you kind of look better than some of the volleyball girls. God, how did you keep this hidden from me for so long? I've gotta see how big this plug is... Can I take it out?"

Rose peeled your panties down and gasped as your plug and "the cutest balls she's ever seen" popped into view. A moan nearly escaped your mouth as you felt her run her fingers over your plug and ball sack to cup your caged package. You tried to relax as she gently stroked around your hole and cheeks with her hands, alternating between squeezing your ass and lightly pulling at the base of the plug, asking you to push as she pulled, only to let it slip in your ass again a few times as she struggled to grip it. You eventually let out a bit of a whimper, which made her laugh, and she let you pull your plug out by yourself with a very satisfying *plop* as your ass let it go.

"That thing is huge! You really are going to let me fuck your ass, aren't you... I mean, I know we said all those things, but it's just a lot... Your poor little butt looks so lonely without something inside it though, do you want me to fuck it now?"

"Yes please! I was thinking you could play with my butt, and then let me out?"

You didn't really mean to agree so enthusiastically, but it just kind of slipped out. Plus, she was right... Now that you had taken the plug out, it was now or never if you wanted to actually be able to finish and not have it be too painful. Rose giddily circled around to the head of the bed and let you help her into the harness, with a 7 inch brown dildo now protruding from her crotch directly into your face.

"Why don't you spit on it, babe?" she said, giggling as she reached her hand out for you to pass her the lube.

"Ha ha, very funny..."

"Okay fine, but get back on the bed like you were and I'll give you what you want..."

Your hands and knees on the bed, you could hear the sticky sound of Rose stroking the lube onto the dildo and she playfully smacked it against your hole and ball-sack a few times, giggling as she teased you.

"You know, your ass does look really fuckable all oiled up like this... and your cage makes your balls look like such a cute little mouthful! I wanna just gobble them up!"

Rose bent down and slurped your balls into her mouth for half a second as she slipped a finger into your butt. The combination sent a shiver through your whole body, and a long strand of pre-cum leaked out through your chastity cage as your body bucked. Her fingers worked your insides vigorously, and it felt just as pleasant as when your mom did it... if not more so, and all you wanted to do was be able to jack off as she did it, but your cage and a bit of pride stopped you from trying. It took so much concentration that you weren't even really listening to Rose remarking at how well your ass was taking her, and she must have noticed because before too long she got tired of using her fingers and gave you a taste of her cock! She had the tip and first few inches in you on her first push into your ass, which definitely got your attention.

"Oh shit!"

"That's right Chris, how does my dick feel in your cute little ass? You just ate my fingers up a second ago, and I saw that fat plug you just had stuffed inside, don't act like you can't take it now!"

Her thrusts were fast and shallow, confirming every word as she opened you up. The sensation of having Rose use your ass was overpowering. Your whole body was shaking with pleasure, and as you tried to think of something to say back to her, she slapped your ass so hard your grip slipped on the blanket and you pitched forward, pulling Rose down on top of you, sending the rest of her strap-on into your guts! All you could manage was a, "Ugh!" as cum spurted out through your chastity cage onto the bed, your legs curling up behind Rose's ass in protest of having your butt stuffed so suddenly and completely.

"Oooo I didn't know you wanted all of it so badly Chris... You want me to really dig you out, huh? Fine, I'll give the naughty boy what he wants!"

Laying on top of you, Rose started pumping her hips, drawing out every inch she could with each stroke to "dig you out" all while you were trying to recover from the orgasm you just had. Unable to form the words to tell her you already came between the grunts, "fucks," and her teasing, you just had to grip the comforter tight and let Rose ravage your poor asshole; your squirming legs and feet taken as a signal that you were enjoying it, rather than pleading for a break! After about five minutes Rose was out of steam and leaned back to survey the work she'd done, and to pull her well-used cock from your well-fucked ass. Her hands spread your cheeks apart to let her see just how loosened up you were...

"Wow Chris... your butt actually looks really fucking good with my cock in it, I gotta say! It's all pink and flushed... Oh, babe, why didn't you tell me you came? There's so much! How many times did you get off?"

Her strap-on slipped out of your ass as she dismounted you, and as you rolled over you could see she wasn't lying about how much cum you had sprayed all over the bed. It looked like a volcano had erupted near the edge of the bed... which must have been from your first orgasm when you slipped earlier and got all seven inches in once surprise thrust, but there was also a very wide stain where you had clearly bust a nut, or just leaked everywhere, while Rose was giving it to you rough; spreading it around as you humped into the mattress. It was all over your crotch and thighs too, so Rose went to the bathroom to get a washcloth you could clean up with before she finally let you out of your cage like she had promised.

"Here, use this to get all that off of you. I think you've earned some time out of your little cage, don't you think? I want you to be nice and clean, and to be able to enjoy this as much as I just enjoyed you!"

Rose laughed at how tentatively you cleaned yourself, and how excitedly you presented your crotch to her when she showed you the key. Your dick was bruised and raw from straining against its captor, and your balls felt like deflated balloons, but you couldn't wait to finally get some freedom, much less a touch from a girl beyond your mom's thorough exams. It only took a second to unlock the cage, and your manhood finally felt free air again, and Rose couldn't help but give it a few little kisses since it looked so abused from the ordeal. A few kisses on each thigh, then she started licking at your balls and soft shaft. She took all of you into her mouth, gently sucking on your tip as she palmed your ass cheeks. You knew she was trying to get you hard, rather than trying to get you off, but while it felt so divine that you started to worry you wouldn't make it, even after all you had already been through tonight. Seeing your face, and maybe tasting a bit of pre-cum, Rose backed off and stood up to pull her shorts off.

"Oh, looks like our little guy is waking up a bit! I know a place that will make him feel really good... Do you think he wants to go there, Chris? I think if you lay down he may get a chance..."

Laying back on the bed, you didn't feel too impressive. Free from the cage, you only stood maybe 4 inches high, and you tried not to notice Rose's smirk as she crawled over the top of you for a kiss, which you thoroughly enjoyed as her lips met yours. Her tongue danced in your mouth as she rubbed herself against your semi-flaccid, and still very sore, dick, but the discomfort you felt slipped away as Rose's wetness started to draw you in. You had obviously fooled around, but you had never actually been inside of her before; so as she rubbed her clit and outer lips against you it felt more and more like heaven. Rose was making cute, little sounds as she humped you, and that's finally what got you back in the game. She felt you stiffen up and kissed you again before sitting up and guiding you into her pussy, or at least holding you still while she enveloped you in one motion.

"Rose... you feel so... warm! And so... good! I love y..."

"Shhh Chris... let me take care of you."

Rose leaned forward to kiss you, but your dick slipped out as she got close, so instead all you got was the flash of disappointment on her face before she sat back on your cock.

"Okay, there... Now let me do all the work, you just lay there and look cute. You were such a good boy earlier..."

She started grinding on your dick, not really riding you, but she was alternating between clenching her muscles and humping your entire crotch with her own, careful to not let you fall out again. After a few minutes, your balls start feeling a deep ache as Rose is getting more and more into her own world, her cautious grinding giving way to increasingly powerful lifts and drops. Each drop slammed into your groin with a loud *clap* and for every moment of ecstasy you felt, Rose's near orgasmic ferocity brutalized your balls; which had pulled tight to the base of your penis due to how much cum they had already expended in just a few hours. Just about as you had to ask Rose to slow down she gave you one last crushing thrust and rubbed out her orgasm with one hand while she sat on your battered dick. It had been bent oddly a few times once she lost control, and you weren't even sure if you had even came yet, at least physically. You're sure you felt yourself try to cum, but it didn't really feel like anything came out, and your balls were aching at both their **** and their desire to push out one last drop of cum. Rose slid down your body and took them in her hand before sucking your penis into her mouth and began flicking the tip with her tongue. It was so tender that your back arched and you started to writhe on the bed, but her hands pulled your back down by the balls as you felt the smallest drip of cum spurted out into her mouth.

"Mmmm! That's a good boy... You were so good Chris. I'm gonna clean up, why don't you get tucked in and I'll be back before you know it!"

Rose gave you a kiss on the forehead before skipping off to the bathroom, no worse for wear, while you felt as dry as an old raisin; and it was all you could do to moan your response and crawl under the covers. You were out in seconds, and had no idea what Rose decided to do in the bathroom before finally joining you for the night... Or what she ended up stealing from your mom's toy collection...