Her Forever Virgin

Margo and Cyrus have learned a lot together over the years. One of the first things they ever learned together was a new appreciation for end credits. It was a week before their prom and as names floated upward an oblivious teenaged boy had to be bluntly made aware of every flirtatious advance he'd missed. From that moment a tall brash teenaged girl learned that the best way to get what she wanted was to take the lead. He said yes even though he had someone else in mind and she kissed him even though their date wasn't for another week. Soon one kiss turned into making out and together they had a new found appreciation for end credits.

They've grown a lot since then but they still carried on their mutual appreciation along with other things. It helped that they were the only ones in the theater, apparently no one else is interested in watching a 2-month-old horror movie at 10:15 in the morning.

Just like I'd hoped,

thought Cyrus as he was locking lips underneath Margo. Cyrus, being only slightly taller than Amy, was towered by Margo which was part of the fun for him. The other part of the fun was feeling his small penis pointlessly try to escape confinement. It was uncomfortable, but to Cyrus it was a good kind of uncomfortable.

Margo pulled her lips away, "So your place or mine?"

In the faint glow of the theater screen, he shot her a quizzical look, "You know I live by myself now, right?" That wasn't his real motivation. Ever since the girls started living together it was slightly strange at first to hook up and spend the occasional night one bedroom away from his high school crush but he got over it quickly. His opinion of Amy's appearance never changed but he'd lost interest in ever having a relationship with her. After all she'd never shown interest in him. He just walked forward and never looked back.

Why did Margo have to drag me back there?

If anything, Friday night made things way worse than they'd ever been in his mind.

"Alright then," Margo couldn't think of a reason to argue. At the moment, she was a bit more interested in helping herself right now rather than Amy. There'd be plenty of time for that later. She lowered her head and they went back at it like kids.

That's the feeling she loved most on their dates. Even to two youths, it became quickly apparent they didn't have a real romantic connection, even if it took them a whole summer to admit it. It still felt good to be together though in a way which emulated the sensation of romance, so that's how she convinced him that there was nothing wrong with continuing to go out and fool around.

A hand slipped up her shirt, appreciated her developing abbs and gently squeezed a bra covered breast. She responded by placing a hand over his crotch.

"Oh fuck," he said as she discovered something harder and slightly bigger than what she was expecting.

"Cy?" he turned to the screen when she said his name, she couldn't help but to give the biggest smile, "Are you wearing a..."

"I'll tell you later," he nervously faced her, "Just not here 'kay."

"Okay then," Margo couldn't believe her luck. Cy was the only guy she knew that could qualify for Amy's magic cage but she never thought he could be so perfect for it until now. She didn't push it any further, she'd just wait until they were back at his place.

Back at Cyrus' they went straight to the bedroom. When it came to sex Margo always led with Cyrus following, though what it meant for Margo 'to lead' had changed overtime. Laying over Cyrus, the both of them still fully clothed save for their shoes and socks; Margo did exactly what Cyrus had been dreading. She reached into his unbuttoned pants and through the fly hole to pinch his tiny restrained penis.

"So, mind explaining this?"

Blushing, he closed his eyes, took a deep breath and said, "It's called a..." he stumbled, too afraid to say two simple words.

"Cock cage."

"Well, I was going to say chastity device but yes. I'm sorry if it's a little too weird for you."

"How did it feel back at the theater?"

"What?"

Margo fell over to Cyrus' side to lay down more comfortably, her fingers still pinching the little resin jail, "Was that little nub," the way she said that last word brought up familiar feeling of shame and arousal, "pushing against that tiny cage back at the show?"

"Practically the whole time."

Margo craned her neck down to his ear and whispered, "That's fucking right. It's so hot to find out I was punishing you that whole time and didn't even know it. I don't know whether to thank you," she paused and gave him a stern shot, "or punish you, Subby," and with that demeaning title Cyrus knew what he had to say next, it'd been too long since he last said it in person.

"Goddess," Cy said with an adorable big grin and a soft laugh, "you know there one in the same to me."

Not quite the response Margo had anticipated but she could work with it, "I guess I'll just have to punish you harder then, Subby. Mind if we do a little role play?"

"Anything you desire Goddess," she could hear in his voice that he was totally invested now, total devotion, "What did you have in mind?"

"Just a first date scenario."

"You're too kind to me, Goddess," a translation from Margo-Cy speak dear perverts, 'Gee thanks, my favorite.'

Cy was about to lift himself from the bed when her hand went from his crotch to his chest, "Where do you think you're going?"

He broke out of the foreplay with his voice, "To unlock myself?"

"I don't remember giving you permission to unlock yourself," she heard Cy gulp which turned her on just that much more, "I want to make it part of our game, my silly little Subby," reaching under his jaw she pinched each cheek and leaned into to rub the tips of their noses together before releasing a slight chuckle, "You'll be lucky if I let you take it off at all."

Cyrus really hoped she didn't mean that but at this point he figured it was a possibility. He wondered if he should tell her now or afterwards the real reason he was wearing it. She gave him a peck and he decided later would be better.

Margo would genuinely hate it if I spoiled the moment.

"So, new names?" Cyrus tried is best to sound sexy, or at least what qualified as sexy to Margo's ears, but he felt like he failed.

"Sure. Samantha. No wait," now Margo found herself out of character laughing and uncertain in simple choice, "How 'bout just Sam or Sammy. I don't know you choose."

Her laugh infected Cyrus until they both died out, "Well Sammy," he emphasized, "I'm glad you came home with me from the wherever," Margo smiled at his cheesiness and he remembered she was so much more than just sexy, "In case you didn't catch my name, it's Elliot," he'd found his new name while she was saying hers.

"Elliot," Margo said lovingly as she pulled Cyrus' arm to bring him over herself, "you're so cute," she started pealing his shirt off, he rose standing on his knees to do it himself, "I can't wait to feel that sweet dick of yours."

"Oh, um, about that..." Cyrus genuinely didn't know what to say. He'd never heard of anyone just hooking up while locked before. Briefly he thought about how he could have found out Friday but he avoided that. If only, dear perverts, Cyrus were acquainted with the author of this book then, he could know exactly how that situation plays out.

Margo decided that 'Sammy' was the kind of excitable girl that wouldn't give 'Elliot' time to respond. She pantsed her partner to reveal his tiny caged cock. Margo covered her mouth with en expression of shock which had been planned as an act but became more honest once she processed what she saw, "What the hell is that pink thing around your dick?" Cyrus covered his face with both hands. Margo couldn't tell how much of it was play and how much of it was genuinely embarrassment, she never could tell with him. Either way she figured he was still enjoying it and this was certainly the most interesting role play session she's ever had.

Cyrus decided that it would be alright to bring in a little truth, it wasn't as if Margo wasn't well aware of it. "It's called a chastity device. I wear it because I'm such a fucking prejac sometimes I can't even contain it in my pants."

"Well, I can't say I'm surprised," she slipped her legs out from underneath him, "I've always heard small guys don't last long," she sat up, leaned forward and flicked it, "at least the cage makes it look a little bigger," Margo swung her legs over the bed and stood up, "Sorry but I'm just going to go. I don't think you can help me."

"Please don't leave!" he cried out in false despair while pulling his pants back up.

Margo turned her head with a grin. To her, there was always that moment in their private improv shows when she felt they'd truly become the characters. Tonight, his plea was that moment, he could see it in her eyes.

She put on a crooked smile, "Well, maybe there is something you can do for me. Get up and take off those pants."

Cyrus got off the bed and stripped what remained of his clothes. He covered what little there was of his masculine shame with his hands. For as long as it'd been since there last session over 4 years ago it'd been even longer since he'd felt genuinely humiliated by Margo but memories of Friday night made it feel real again but in a good way. Somehow, having his 'biggest' insecurity attacked by Margo made him feel desired. It never made sense to him but he knew he liked it so he didn't fight it.

Margo has always enjoyed the sense of control she has over Cy even before she knew it herself but something about looking down at the little pink cage around his cock made her feel more powerful than ever. There was just one thing missing though to make her experience whole, "So how does that thing come off?"

"I have a key to unlock it," she loved the shaking in his voice.

"Give it to me," she said without hesitation.

"What?" She couldn't tell if he misheard her or if it was part of the game but she liked it. It was the kind of response that would give her an opportunity to up the stakes. She repeated the demand to him, this time emphasizing each word in the sentence threateningly. He gave a gulp, nodded and turned to go retrieve it. At the site of his bare ass facing her she slapped a it which caused him to gasp and jump a little in place, before he speed walked to his desk and pulled something out of a cabinet. He returned with a key on what was clearly a convention lanyard meant for an ID and handed it to her.

"Seriously?" she broke character.

"What?"

She stuck her pointer fingers In the lanyard and stretched it out, "We need to get this key a better accessory."

The ever-practical Cy rolled his eyes, "Yes Goddess."

Well, that confirms one suspicion,

Cyrus smirked while trying to get back into character. He couldn't look her in the face which only added to his embarrassment which in turn only added to his arousal. Even though Margo was clearly into it, he still felt a sense of shame about his cage, he couldn't tell if it was real or part of the role play but he hadn't felt this exposed around her since the first time she saw him naked.

Margo slid down her bottom wear to reveal her vag, "Eat it," Margo commanded softly. Cyrus had to crouch down to start eating her out. It was a bit uncomfortable, especially after getting so used to being with his ex, Shri, who he could get on his knees with. But mild discomfort wasn't going to keep Cyrus from doing his job. He placed a hand on each thigh and went right for it like a starving dog. He knew Margo was the kind of girl that loves to jump right into rough stuff. His tongue rediscovered her flower as his fingers caressed her thighs. He took in her moans in a kind of egotistical arousal indicating he was doing his job right meanwhile; he felt the constant reminder of his nub pushing against confinement.

Cyrus suddenly felt a grab of his hair on the back of his head, Margo pulled his head out and downward to force him to look up at her. "This isn't your first time eatin' pussy, is it pin dick?"

She tried shooting down a cruel grin. In reality she needed a break before her legs brought her collapsing onto Cy. Besides, a little edging was good, it only made her more eager to put him back to work. He timidly nodded yes.

She ran her fingers to the top of his head and grabbed a new patch. Then she forced him to stand and walked herself backwards into a wall. Leaning for support she forced him back into her moist crotch. He pressed against her body so that his tongue could reach more deeply. He didn't settle on one spot instead going up and down. Then he brought in two fingers. Margo decided she didn't want build up anymore, she wanted to get right to the main event. "Kiss my clit!"

Before she knew it he was putting the full attention of his mouth onto her bean as two more fingers entered her vag. His fingers were much more thoughtful than his tongue. She was happy to see he still remembered how to navigate her body. With his other hand he started at her knee with the tips of his finger, slid up and around to her thigh and finally the bottom of her ass. "Naughty boy! I didn't give you permission to touch that," Cy paused his task to listen but stayed in place, "Go ahead, you already broke the rules," she Gave a light disciplinary slap on his head, "I'll just punish you later. Now back to it."

Margo enjoyed looking for any little opportunity to punish him. She was being unfair and proud of it. Life wasn't fair so why should she be fair to him?

This is the one time I can be unfair; he loves it unfair,

she remembered deviously as she neared orgasm. Her grip on his hair tightened, "Don't stop!" Cyrus used his lips and tongue to spoil her clit, "Eat that pussy pin dick!"

Cyrus knew what it felt like to please his goddess, but it had been a long time since he smelled its fragrance or endured real pain for it or even felt it in person. He kept going, he knew one orgasm wasn't enough for her. He slipped out his fingers and went down to caress her deeply with his taste receptor. His moist hand began playing with her thigh.

He felt her grip on his hair again, she was about to make a commandment. "I still need to punish you," she said tauntingly. He rolled his eyes up to see her top landing on his face. He pulled out to let it fall between them and looked up again at supple breasts, "Go bend over the bed!"

His head hung in shame as he stood up when she gave him another reason to look down. She pinched the head of his cage between her thumb and forefinger, "Look at how small that dick is!" Margo followed up with a cruel laugh, "Did you think you could please any girl with this, Elliot? Or maybe I should call you Ellie instead?" Her emasculation gave rise to another doomed escape attempt by his cock, "Do you want out?" Cyrus only nodded yes at the question, "Well guess what, Ellie," she said condescendingly.

"What?" he responded nervously.

"Naughty boys don't get unlocked and you were supposed to be bent over the bed by now. Not standing here letting me examine your tiny dick."

Cyrus gulped, apologized and sped over to the bed to expose his butt for discipline. As he bent over, he couldn't help but to focus on the sensation of denial that came from the shame and humiliation of his goddess's words. He clenched his teeth and buried his face in the bedding in anticipation of Margo's attack. He felt her finger tips gently land on his shoulder, "Oh Elliot, now your trying to behave like a good boy," Cyrus cooed as her nails lightly scratched his back downwards, "but it's to late to save that cute ass of yours!"

Cyrus moaned at the stinging pleasure of Margo's first strike on his defenseless bottom. He felt it again and this time his mind returned to how his wee member was trapped. A third time and Cyrus yelled out, "Oh fuck yes!" as he squirted out precum from his crotch cage.

Margo took a step back to admire how pathetic she made him look. She noticed a line of pre-ejaculate dangling from the head of her victim's cage. "Does someone want out of his cage?" she teased.

"Please!" Cy stressed anxiously.

Margo got on the bed, spread her legs open and declared, "Give me one more orgasm pin dick and I'll consider unlocking you."

Cy dutifully got on the bed and stuck his head between her legs. She leaned her head back and decided she'd just let Cy do his thing. She thought she'd have to re-educate him but it turned out her little Subby still knew his way around her body. She bit her lower lip as he felt his fingers explore her while he made out with her clit. She'd spent years training him to respond to her body. She'd trained other submissive lovers as well but none where ever as good as her original, Subby. He only traveled where he was invited.

She felt his tongue slide up to her pubic mound, between her abbs, around the key and finally on her small right nipple. Margo moaned before commanding slowly through pleasure, " pinch my other nip." He'd already started by the time she said "my" but it was a matter of principle that she finished her decree. Her sub sped up the motion of his fingers as her moans increased in volume until at last, she came for a second time.

Cy rested his head against her chest, heaving deeply she rewarded him with a demeaning pat of his messy hair. "So, Sammy," even with her eyes closed Margo could see the nervous smile he usually gave before asking for something he was uncertain to get, "can you unlock me?"

"Let me think about it," Margo pressed a finger against her chin, "I thought you were being a good boy after the way you ate me out, but then you had to go ask about release," Cyrus loved their game but was going to have to put his foot down if she was seriously going to deny him any longer, "However, I'm feeling generous so I'll let it slip, this time." Cyrus didn't want to express it physically but in his heart he was giving a sigh of relief. Generally speaking it was never really a great idea to argue with Margo but he especially didn't want to argue about this particular subject.

"Thank you!" Cyrus turned inwards and kissed her small breasts in random spots as worship, "You're too kind," he added pathetically.

Margo removed the lanyard from around her neck and held the key, "I want to unlock you."

"Yes please!" Cyrus couldn't contain his smile. Something about watching his ex, Shri, unlock him made him feel special. The pair readjusted so that Cyrus sat upright in the bed with his legs spread open with Margo laying on her stomach to have a better look at his cage.

"Where's the lock?"

"What?" then Cyrus thought she might have expected a pad-lock, "It's internal, look on the side."

"Where? It's a little hard to see because of the size," Cyrus couldn't tell by her tone if that was intentional or natural but regardless his mind processed it as an erotic insult which caused him to twitch in his cage, "Hold still, I still need to find that hole," Margo pinched Cyrus' tiny cage to find her target, "There it is. So how do I unlock it?"

"Just turn it up and pull it out."

"Real talk," said Margo placing the key in, "Why is it pink?"

"My ex told me they sent the wrong color," Cyrus rolled his eyes at the memory of opening the package, "but the receipt said otherwise."

"You're too forgiving," chuckled Margo as the lock slipped out, "So are you ready to be free, Elliot?"

"Please set me free, Sammy," he felt the resin cage shed off his tiny member allowing it to spring to life and then carefully popped his aching balls out,

definitely not her first time playing with chastity.

Just then, Cyrus felt a sensation entirely unfamiliar to him. It was the moist vacuum of Margo's mouth which overwhelmed him in what he could only hope was at least 10 seconds. "O-ma-gawt!" blurted out Cyrus in bliss as he grabbed his hair. His goddess's mouth held on to his prick despite the spasming hips. Margo seem to be the only person who understood how weird his condition was and she would occasionally come up with new tests. This continuous blowjob is probably her latest one. He could feel her gulp his seed as she continued sucking.