Her Forever Virgin

"God, I don't think I've done this since you moved," Amy struck a lighter and inhaled smoke from the bong she held by the neck. She coughed clouds of smoke as she passed it off to Cyrus.

"Could've fooled me," chuckled Cyrus before taking his own hit.

Amy was still trying to clear her throat before getting out, "I can't believe I let you talk me into that."

"Since when was asking one time considered talking you into it?" Said Cyrus, placing the bong and lighter on the coffee table in front of them.

"Shut up!" she slapped him playfully on the chest and rather than retracting her hand she instead slid it up his shoulder and squeezed gently. She pulled him in closer and she leaned in and they shared their second kiss of the evening. The first had been in Cyrus's car after dinner. It was just a peck then, initiated by him to make sure the date was going well. This was different though; it was longer and filled with desire.

When the date started Amy told herself this was all just part of the plan. Margo told her just to treat it like a regular date after all that's what it was to him. The plan that she an Margo came up with, well actually it was really just Margo's plan, was to get him naked and embarrassed so that it would be easier to convince him to wear the cage. Sure, it was easy on paper but incredibly nerve-racking to actually do in practice. Amy was also a little worried that Cyrus wouldn't find her attractive enough to cum prematurely though Margo said she'd give her $300 if he didn't, she was that confident.

She finally withdrew from him. Each looking into the others eyes Cyrus asked, "Do you wanna go to the bedroom?"

What did I just say? That was the exact opposite of what Cyrus was supposed to say. What he had meant to say since this date started was something like, thanks for the great dinner or I think I'm ready for bed. Sure, it wasn't a terribly explicit question but how else could it be interpreted? He held on to the hope that maybe she'd just say no in someway. Painful yes, but a lot less painful than if she were to later on reject him for his manhood or lack there of.

For a few brief seconds he clung to the hope that Amy wouldn't be interested. She broke eye contact with him, look to the left, and said "sure," with a slight shrug.

"Cool," he really wished he could have said something better than that. Taking a nervous leave, he took her by the hand and started leading her in the bedroom. Cyrus opened the door slowly and with a gesture invited her to go in first. He took notice of how her ass swayed as she walked over to the bed and took a seat.

"Are you coming?" She padded the empty space next to her.

"Yeah," Cyrus winced, he felt a familiar sensation on his crotch, though probably not the kind you are thinking of dear perverts, "I just got to use the bathroom really quick. Be right back."

"Okay, I'll just get ready then," she responded in a soft voice.

Cyrus started heading towards the bathroom. He checked his pocket for his keys and remembered He had left them on the coffee table next to the bong. He ran to grab them, then mad his way into the bathroom and locked the door behind him. Cyrus actually had no need to relive himself. He unbuttoned his jeans and lowered his pants and underwear. At this point he knew there would be no hiding his embarrassing micro penis or avoiding the shame of an early ejaculation from his old crush but at least she didn't have to find out the extent of his sexual problems.

He looked down at the small silicone cage around his cock, put the key in and turned and slid out the internal lock. As Cyrus slid the cage off his cock he started thinking about how much it had been bugging him all night but it was worth it. The alternative was risking having public embarrassment and even though he didn't feel quite the same about Amy as he did in high school, he still thought she was one of the most beautiful women he knew. He popped his balls through the ring and then removed that too. Every time he did that, he was reminded of how his average sized testicles made his dick look even smaller. He put the two pieces back together and relocked it and hid it away in the medicine cabinet.

Upon closing the cabinet, he stared at himself in the mirror and reflected on his evening with Amy up to this point. He had been scared at first and was worried that the date would go terribly but it didn't, at least not yet. While the idea of going on a date with his high school crush head reignited the flames, actually going out with her extinguished it. What had once been just a teenage boys crush had now been replaced by a more tempered enjoyment of her company. They have hung out before of course but something about those old emotions prevented him from seeing her entirely as just a regular girl. The Amy he saw now was somehow more beautiful yet also more approachable.

As Cyrus pulled his pants back up he thought about how he could still say no. There was no rule that said he couldn't go back if he already said yes but deep down he knew he at least wanted to see if she'd give him a chance. More than anything he was hoping to at least be able to please her in his own way.

Cyrus realize that he was beginning to psych himself out so he turned on the faucet and splashed his face with cold water to bring him back. He took a deep breath and headed back to Amy.

Amy was glad Cyrus left the room. The first guy she was ever with wanted to watch her strip naked. At the time she didn't really know what he meant so she just undressed casually which he said wasn't as sexy as he thought it'd be. Amy internalized that small comment and ever since then she's never felt comfortable undressing in front of a partner. Two of her exes told her it was a weird quirk but they didn't care and somehow it felt more comfortable being strange than taking off her clothes in front of people. She's largely gotten over it but still would rather undress in private.

As she lifted up her top, she was reminded of other developments that made her unhappy. Margot wasn't lying to Cyrus when she said Amy hadn't been with anyone in three years. Ever since inventing the Your-Favorite-Flavor-Cup she lost a lot of free time because of its runaway success and her refusal to share the charm she came up with. Once she found out how to manage her time, she just never really connected with anyone again. It wasn't that she didn't want a relationship but it just wasn't really a priority for her at this point in her life. She'd noticed it before but now it was especially a parent that attitude had an effect on her body. Holding her top in one hand she looked at her midsection and couldn't help but to focus on the layer of pudge that wasn't there the last time she was with a guy. Removing her bra reminded her that she was at least mildly happy with her C-cup breasts. She never really knew why guys are so into them but she had to admit she enjoyed when they got attention.

Moving down she was reminded of more things she didn't like about her body. As she slipped her jeans off, she was reminded of all the times Stacy made fun of her big butt back at witch camp. It didn't help matters that she lives with the memory of Stacey making it comically large during a transmogrification lesson. Stacy may have gotten a week's detention for that stunt but Amy is the one who lives with the memory of all the other girls laughing at her the rest of that summer. Stepping out of her jeans she was also reminded of how she didn't like her accompanying thick thighs.

Amy turned to the wide-open door as she was curious as to why she was hearing so many footsteps when he said he was just going to the bathroom which was right next to the bedroom. When upon hearing the distinct noise of a slamming door she returned to undressing.

Looking down again Amy bit the tips of her fingernails. She realized her bush is so large and unkempt that it poked out her panties. It wasn't the first time she noticed. It began with telling herself she'd take care of it tomorrow, and then eventually until she really needed to and now It dawned on her that time should have been the shower, she took this morning but then again she never expected to be doing this when she woke up. Removing them only made her feel worse, it gave her full view of her neglect so she raised them back up.

Stripped down to nothing but her socks and panties she walked over to a desk in the room and placed her clothes on it. She turned and looked at herself in a mirror built into the closet door. Staring at her reflection she decided that while she wasn't happy with her body, she also didn't hate it. As a witch Amy did have the option to transform her body into something that she would be happier with but such modifications were generally reserved for real malformations and considered a social taboo for frivolous things. With vinegar in her mind, she thought about how it didn't stop Stacey from modifying her body to have a modeling career.

She went back to bed and sat in nervous patience for Cyrus to get back. Twiddling her thumbs in the nude she began to think back on the fun evening that let her up to this moment. She still didn't know how she was going to bring up the subject of the chastity device to Cyrus or even how to tell him about magic but that wasn't really what she was thinking about right now.

What had started out as a mission may have turned into a real date. Besides, to Cyrus it was a real date, albeit a casual one. It was different going out with someone she considered a friend, she learned how little they actually knew each other. Looking back on her memories since high school she realized that she'd never been alone with him.

In high school, they were a part of a fairly large friend group comprising about a dozen people. In a group that large there were always bound to be people you just don't get as close with but as people moved away or found new friends in adulthood, Cyrus had been as much a constant as her friends Margo and Jake up until his move a few years ago. For most of her life it was usually just the Amy and Margo show and she was always happy to watch whatever new art house film Jake was just heard about with him but she never just spent time with Cyrus. She wondered why that was, especially after how much they talked over dinner. It was the mix of being reacquainted with the familiar and also little surprises here in there about him that made it fun.

In the past most of the guys Amy dated were dudes who thought they wanted a relationship but really just wanted sex and the girlfriend experience. Cyrus was different, he was very clearly enjoying their conversation and he wasn't rushing to this moment like the other guys. Though if what Margo said was to be believed there might be another reason for that. Amy also began to consider that it might have gone so well precisely because it was a casual date. That's gotta be it.

"Oh, wow I didn't expect you to already be undressed," Amy turned and saw Cyrus blushing as if though he'd walk in on her without permission, "You're incredible."

Amy couldn't help but smile at the hyperbolic compliment. More like average at best. "So um..." Amy lifted her knees and wrapped her arms around them, "are you going too?"

"Oh yeah," his hands shook as he removed his shirt. His eyes were shut tight as he removed both his pants and boxers. Amy was starting to feel like she should stop him. It didn't ease her guilt considering what she's here to do.

But before she even recognized her thoughts as guilt his pants fell to the floor revealing the tiniest penis she's ever seen, Margo wasn't exaggerating. It couldn't have been more than two inches long plus, he was dripping precum and twitching. Amy dipped her head to conceal a smirk although she failed to suppress an audible snort. He opened his eyes again but he was clearly having trouble reestablishing eye contact. After examining her body Amy had hoped to get this over with only really having to show him her breasts but she decided to drop her knees and put herself in full display. She hoped that be enough to make him comfortable because at this point, she really didn't know what to say but she didn't want him to feel ashamed just for being himself.

Cyrus gulped, "I'm sorry."

"For what?" at that Cyrus wondered if Amy really didn't notice, really didn't care, or maybe she was just trying to be nice and find away to talk herself out of here. In what sounded like an angel's voice to Cyrus she said, "Why don't you come over here?"

With each step Cyrus could feel himself coming closer to climax just from looking at her. He bent down and kissed her on the mouth. She kissed him back this time locking lips. He leaned forward and she went backwards on to the bed. Cyrus couldn't believe he'd managed to last this long with the most beautiful girl he's ever been with. A sudden idea formed in his head. He spent all that time as a stupid kid fantasizing about losing his virginity to Amy but maybe that's actually how it was going to go down, even if it turned out to be at the age of 29.

"Oh, fuck me!" Cyrus felt the all too familiar sensation of orgasm but it wasn't encased inside Amy, rather it was just the tip of his lesser head rubbing against her thighs, "Sorry."

"It's okay."

While most gals in Amy's position would be disappointed in their partner, she was just thinking about that $300 she wasn't going to see. Cyrus lifted him self off her and walked over to the night stand and pulled out a piece of tissue from a box. Amy sat up again.

"Let me clean that off," he said in a meek voice. Amy didn't know what to say in response, she started to think about how to ask him about the cage. She laid back down and stared at the ceiling while Cyrus balled up the paper and threw it away. Amy realized she should have thought of what she was going to say instead of winging it.

Relaxed in body but stressed in mind she was a little taken aback when Cyrus mounted her again. Is he going to try again? He put one hand behind her head and went down to make out. Amy figured he probably just wanted to enjoy the intimacy of the moment a bit longer and after a lovely evening she was more than willing to oblige him. Then unexpectedly his lips left her own and went to her left cheek. Then, three soft kisses along her neck, some more on her chest, a short suckle on each nipple, and downward he went like a skipping stone along her stomach until he stopped at the front of her panties.

Horror dawned on Amy as he slipped his fingers through the side of her panties. She was afraid he'd say something or be grossed out. I should tell him he doesn't have to, she thought but she was also really enjoying the moment. His smooches zigzagged down her thighs as he pulled off her panties.

She decided that this had gone far enough, "Um Cyrus..." she was silenced as he started to work her clit with his tongue. She began to moan, Amy forgot how good it felt to be pleased by someone other than herself. She felt two of his fingers gently slip in the lower part of her vag.

Cyrus couldn't believe this was actually happening, she tasted like paradise. With his free hand he began to slip his fingers under her right ass cheek, she lifted her hip slightly to give him easier access. He squeezed it lovingly. Cyrus replaced his tongue with his thumb which caressed her clit in a circular motion.

"Are you enjoying it?" Cyrus asked panting, his forehead pressed just below her navel. Amy was so taken with pleasure that she could only let out an affirming vocal sound through her moaning. Cyrus let go of her ass and began moving up ward with his hands and head, all the while his other hand still admirably preforming its duty to ensure that the pleasure didn't stop. With his free hand he started pinching her left nipple while with his mouth he began to suck on the other.

At first Amy was reminded of how nice it was just to be with someone else again but now she was wondering if sex had always felt this amazing. Her mind a haze from the pleasure and flower she smoked earlier she couldn't tell how much time as passed since he started on her clit. For just the briefest fraction of a second she understood how time was an illusion before losing it as waves of pleasure began to crash against her body. For someone who came so quickly he sure knew how to make the good times last.

As an intense sensation began to build in her nether regions, she knew what she needed but she could hardly muster the strength to ask a coherent question through her vocal bliss. With one hand she pulled on his hair and began pushing him down.

Cyrus loved having his hair pulled and petted during these moments, he couldn't believe how in sync he was with Amy. He allowed himself to be pushed back down to her delicious pussy. At first, he was pushed slightly below her clit, he pulled out his fingers and began to lick deeply.

Amy had meant to bring him back to her clit for a little more stimulation but she was really enjoying what he was doing a little deeper down. He wasn't just using his tongue; he even used his soft lips to add just the slightest but much appreciated extra pleasure. She let him remain their awhile longer before she was ready for what she really wanted. She tightened her grip on his hair and pulled him up slightly. His fingers returned to their place while he returned to her clit, this time sucking it has he had her nipple. Amy couldn't believe what was about to happen, it'd never happened with any of her previous lovers after all.

"Oh yes! Fuck yes!" she yelled. Cyrus felt flesh enclose around his fingers then loosen as her womanhood flooded with her feminine juices soaking on to his tongue. Her grip loosened and fell away from his head. As often happened in these moments he'd gotten so into focusing on his partner that he hadn't realized he was hard again and began shooting off his premature load onto the floor. He gritted his teeth to resist making any noises of orgasm.

Both of them were left breathing heavy. He took a seat next to her on the bed. She lifted back up and gave him a small kiss on the cheek. "Do you want to cuddle?" he asked. Amy gave a single nod. They went under the sheets and fell asleep feeling bare skin against bare skin.

In a morning drowsiness Amy wondered why her pillow was so hard. It was comfy-ish but not quite the softness she needed to forget about the day to come and sleep in. Then she heard the snoring from above and realized she was on Cyrus' shoulder. Amy thought she'd just enjoy it a bit longer and closed her eyes to find Mr. Sandman again but her eyes opened wide as she remembered why she was here at all.

How had a plan to get this poor guy to wear a chastity device go so wrong in all the best ways? Amy felt a sense of shame about her plot. Carefully she got out of bed trying not to wake him. She picked her panties off the floor and stepped into them as she walked over to the desk for her clothes. Quietly as she could, she started to dress herself.

"Amy?" Cyrus wasn't fully awake yet, he was still lost in sleep even more so than she was just a few minutes ago. He padded the empty space where she'd been. Pointing an index finger in the air she slowly made a Z shape and he went right back to sleep. This spell was meant to help someone get to sleep but if they were just woken up from a full night's rest the effects would at the very least last 10 minutes and a second attempt would end in failure. She left quickly, locking the door from the inside before leaving. She ordered a ride share on her way out of the apartment building and went home.

Back at her place she opened the door to a different surprise. Brando, Margo's only ex that was notably taller than her, was blocking the entrance. "Oh, sorry Annie. I was just leaving."

She thought about correcting him but wondered if it'd even matter at this point. If he didn't bother to learn her name after almost a year of dating her best friend why should he start now? "Bye." She stepped aside to let him out and then entered. All the while her little dog, Terry, yapped in what seem like distain until the door shut. Terry's attitude shifted to her jovial self and she greeted Amy, her paws scratching the pants legs.