Is Something The Matter? Ch. 06

This is Chapter 6. If you want to figure out how these characters got here, you're going to have to read the rest of the series which might take a little while, but I hope it is worth it. If you don't -- and you just want a little story this might be able to stand on its own. Not 100% sure.

Thanks to all for comments, reviews etc. As I mentioned in the past introduction, this thing has started writing itself, and as such there are a few threads from the earlier chapters that I couldn't continue as the story changed. A real author would have started with a story map in place, but I'm not a real author.

There are elements of Femdom, Chastity, Gender Roles, CBT etc in here. If you don't like those, please find another story. Also please recall that since this is a story that includes elements of power exchange, there is mention of using safe words. If you do play -- please do so in a safe, sane, sober, and consensual way.

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Is Something The Matter -- Ch. 06

"Is something the matter? I mean seriously what the heck is going on?" Steve lay awake, his mind racing as the morning light filtered into the room. Last night had been another amazing night in a series of amazing nights. He had fallen asleep as the little spoon to Amie's big spoon while she was wearing a strap-on...and instead of being totally freaked out by it, he was kind of in awe of what had transpired.

He knew that everything Amie had done in the last 24 hours had been painstakingly planned and deliberate on the part of Amie, and he also knew in his heart that the seeds for what had happened had likely been planted weeks before. Amie was good. He thought he knew her, but since they really started playing with chastity in the Spring of the year, she had shown him an entirely different side. This was the professional side of Amie -- the one that allowed her to be one of the youngest attorneys in her firm to be on a partner track. She planned, anticipated, led, guided, and then pounced. Only instead of him being some poor sap who tried to welch on a corporate contract, he was her husband -- one who had been introduced to her particular brand of long-term tease and denial and female-led relationship. While he was focusing on the day-to-day aspect of being locked in a chastity cage since early September, she had been thinking days and weeks ahead of him.

And now -- here he was, waking up in a pair of red ruffled panties, a silky camisole. As he looked over to his left, he could see a bulge under the sheets that confirmed to him that Amie had worn the strap-on the entire night as well. How had they gotten here, and why was he totally turned on by the fact that Amie was packing a cock while he was packed into his chastity device. He felt down between his legs and confirmed that he was locked away -- and felt the moisture of what Amie called his 'chastity tears'. He had been leaking like that now for the past few weeks, and nothing short of a full orgasm was going to stop it now, but here he was -- October 29th -- 3 days from release and ALL he could think about was Amie.

He thought about her every hour of the day. He dreamed about her. He found himself typing her name into work documents. Every minute of the day he thought about what he could do to please her -- to help her -- to support her. By taking away his orgasm and teasing him mercilessly, she had given him the greatest gift. The gift of understanding how much she impacted his world. Heck, she had BECOME his world.

Amie stirred, her arm reaching under the sheets. Steve could see her hand move up and down as if she were stroking herself. She was stroking the rubber phallus attached to the strap-on belt. "So, this is what it's like to wake up with morning wood. Honestly, I don't know how you guys walk around with these things." She chuckled, recalling that as a line delivered by the character Elaine on Seinfeld.

Amie stretched her arms above her head, and motioned Steve to slide over and join her.

As he did, Amie slid him into the crook of her arm, with his head resting on her chest. This was a position that Amie had been introducing to Steve. It was a position with which she was familiar, as she had in their previous life been the one cuddled up with her head on Steve's chest and his arm around her. Now the tables were turned, as she had slowly introduced Steve to her being in the dominant position in bed and in their overall relationship. She ran her hand across his back, kissed the top of his head.

Steve lifted the sheets and peeked below, looking at the dildo laying against Amie's flat smooth stomach. "Pretty impressive. I probably should have slept with the smaller one, but I gotta tell you, a girl could get used to having a cock like this. Now I know why you guys are always touching them. Of course, you can't really touch your cock the last few weeks, can you? Well, that'll change soon. Who knows, you might wake up just like this in a few days."

Steve caught that -- what did she mean "who knows? Was she NOT going to release him?"

Amie felt Steve stiffen, and patted him reassuringly on the head. Don't worry hon. I'm gonna let you out. Of course, if the changes I've seen in you as of late are anything to measure by, I'll bet you'll be asking me to lock you back up in short order. Let's talk about that though. I want you to think of something special to mark the unlock. Think of all we've learned over the past few months and let's plan something special to mark how we've both grown." As she said this, Amie gently moved Steve's hand down to her stomach, which was bare as her sleep tee-shirt had ridden up in the night. She left Steve's hand there on her stomach and began caressing his back once again with her other hand. After a moment, she felt Steve's hand move down to the strap-on and could feel it gently manipulating the very lifelike dildo. Amie had been on the receiving end of this dildo a few times over the past few months, and admittedly it was her favorite. She knew at that moment that she had successfully implanted the thought in her love's mind, but she didn't want to push it too far right now. She let Steve caress the dildo for just a bit, and then moved his hand down to her thighs. To Amie, her inner thighs were an erogenous zone, and Steve had this way of just lightly running his fingertips lightly over that very sensitive skin. He took the hint and started caressing her thighs. Amie felt her temperature rise as Steve started to work her buttons. Sadly, she needed to get up and get on a work call. She shifted her body slightly and sighed, letting Steve know that it was time to get up. He took the hint, stood and stretched.

Amie admired him as he stretched -- he looked great in his little panty and camisole outfit. "What do you have on tap today, hon?" she asked.

Steve responded "I actually have to head into the office today and then drop off some papers with one of my older clients." He stopped to think -- he hadn't been into the office for quite some time, and wondered whether his good suit was pressed.

"You can't wear those though hon, people will think you're wearing a diaper."

Steve looked down, his hands running lightly over the rear of the panties, and he blushed.

"Don't blush hon, you really pull that off. If you're wearing your blue suit, I'd suggest you wear the lycra thong. It'll hold your cage in place and you know... no visible panty lines". She paused -- "I'm going to advise that you wear a regular tee-shirt today under your dress shirt. And hey, if you're taking a shower -- don't forget to shave your upper legs!"

Steve headed off to the shower, his mind reeling back and forth between work and some of the things Amie had said this morning. He really wanted to make the end of Locktober special for Amie, as she had put so much work into it. He kept thinking back to some of the conversations they had had... she had really opened up to him this past month, telling him about what she felt during sex, both physically and emotionally. Sex had always been a physical act for him, and other than the love he had for Amie, he never really considered the emotional side of it, but the longer he was locked up, the more he experienced the ups and downs of their physical interactions. He stepped into the shower and started cleaning up for the day, spending a lot of time cleaning the cage. He found a few areas he had missed when he had touched up the shave job on his chest and underarms, and started the touch up job. He looked down and remembered his promise to Amie to shave the upper legs. He grabbed the shave gel and went to work.

Amie was downstairs in the kitchen getting the coffee going. She hummed to herself, reveling in what had happened the night before. She had cleaned and stowed the strap-on and the dildo, and tidied up the basement. She knew she had planted some ideas in Steve's mind, and all she had to do was wait and see what developed. As she sat down to go through email and texts on her phone, she heard him enter.

Steve was looking snazzy in his blue suit. The pants were a modern cut, so they were tight, and she could just make out the bulge that she knew was his cage. If you didn't know it was there, you'd never know to look, but she idly rubbed the key that was hung around her neck and watched as Steve started her morning coffee and toast routine. Gosh, he had a cute little butt she thought to herself.

"So. I've got a busy day" Steve started, "but I'd like to talk to you tonight about the end of Locktober. I've learned so much this month about myself, and you (of course), but also about our relationship. I'll be back from my appointments by 2 o'clock, so I can take care of dinner if you like."

"I like, I like! I'm so damn sick of cooking, so I'm happy to have you strut your stuff in the kitchen, hon." Amie replied. She thought to herself "okay... so he's thinking. Let's see where this goes."

Amie spent the day working, and finally turned around and realized that the clock on her computer showed it to be 4:40. Wow. Where'd the day go? She smelled something good from the kitchen, shut down her laptop and wandered over to find Steve browning some meat on the stovetop. Next to it stood a pot of sauce that smelled of garlic and goodness. Amie admired how he threw himself into the prep, and even the little touches he made as he precisely chopped up some veggies to add to the mix.

They settled down to dinner, adding in a nice bottle of red wine that Steve had purchased during the day, and afterward sat together at the dinner table in silence. Steve finally broke the silence, "Okay so... as I mentioned this morning, I'd like to talk about the end of Locktober Amie, you've done a masterful job of working us through the past few months. Honestly the time you must have taken to think these things through, and to help us get here just boggles the mind. I really thought I was going to safe word on the whole month about a week into October, and you patiently kept me focused and moving forward. Every step of the way, you're two steps ahead of me. You've learned to anticipate, lead, guide, cajole me, and I'm incredibly thankful for it. So... with that in mind, here's my thought...you've obviously already gotten an idea of how you want this to end, and you've been so good at both planning this and also making me feel comfortable with what we do, that I'm going to put it in your hands."

Amie sat there, feeling like the cat who caught the canary. What Steve just said is that he accepted her leadership, and has committed to a wife-led-marriage (at least in the bedroom). "Okay. I appreciate your candor, and I want to thank you for recognizing the work I've put into this. This is a far cry from your claim back in March of 'all you have to do is hold the key!'. There's a lot more to it than that, but it has become my favorite hobby. I'm going to let you know how I want to conclude Locktober, but once I spell it out, I'll need you to confirm to me that this is what you want, and then I'm going to have you ask me to do it, so we not only have passive, but also active consent. That's important."

Steve nodded his agreement, and Amie pushed her wineglass to the side and leaned in. "So, as you've likely figured out already, but are too frightened to admit, I look like a Rockstar with the strap-on."

Steve gulped and the color drained from his face.

"I look like a Rockstar" she continued "and I've started to understand the power dynamic that having a cock between your legs -- or at least a cock that isn't confined to a cage -- can bring me. Now, if you recall we had a conversation a few days ago about the time I realized what it was like to truly have sex. What it was truly like to allow someone you cared about to physically penetrate you. To me, it was more than a physical act -- it was a moment of emotional and mental awakening." Amie paused to let that sink in. "So, here's what I want to do. I want your first orgasm to be from me pegging you with the strap-on. From what I've read online, some guys can't cum from being penetrated, but I'm better after 2 months of denial, a soft wind will get you to explode, so I don't anticipate it being a problem."

Steve nodded. He had figured that things were going in this direction, and he was actually a little relieved that it wasn't anything more humiliating. After last night and this morning and seeing how confident and comfortable Amie looked in the strap-on, he actually was excited to see where this was going. He had never thought about a man, but the thought of Amie, and her flat stomach, perfect breasts and amazing beauty taking him like this was a bit overwhelming.

"Okay so now is when you're going to ask me to do this" Amie said, breaking his thoughts.

"Amie. I love you. I'm so happy that we've gone down this road the last few months. To end Locktober, I want you to give me my first orgasm..."

"Want" Amie asked?

"Need you?" Steve added.

"Try begging."

Steve gathered his thoughts a bit more, cleared his throat and got ready to ask her again.

"Why don't you get down on the floor on your knees and start over" Amie suggested.

Steve stood up from his chair, made sure that the window shades were pulled, and then stripped down to just his panties and his cage, then knelt in front of Amie's chair. "Amie, I love you. I'm begging you to give me my first orgasm out of the cage by pegging me."

"Keep going."

Steve was confused -- he thought he had covered it all. "Please Amie, I want you to make my first orgasm one that I'll always remember."

"And if I peg you like that -- what will you be?" Amie asked.

"I'll be yours." Steve interjected, with just the hint of a question mark at the end of the phrase.

"You already ARE mine. What will you be?"

"I'll be your bitch?" -- again Steve was more asking than answering.

"Okay, now put it all together" Amie demanded.

Steve stopped and drew a breath "Please Amie. At the end of Locktober, I want you to peg me in my ass and make me cum. I want to be your bitch".

Amie then asked "And what about your safe word?"

Steve continued. "I know that I have a safe word and it is 'banana'. I promise to use the safe word if something goes beyond what I can handle."

"Okay!" Amie exclaimed. I accept your request. Please know that I'm going to do everything I can to make this enjoyable and fulfilling for you, my dear. I want this to be special for both of us, and I want you to really understand what it is like to accept someone willingly and lovingly into your body."

Amie stopped and took a sip of wine. "Tomorrow morning, when you get a break from work, I want you to head over to the lingerie boutique. I've asked my friend to put a set of anal plugs on hold for you so you can start getting ready for this. When we get home tomorrow, we're going to start getting you ready so we don't hurt you." She looked down and Steve and ran her hand lovingly across his forehead to push his hair out of the way.

"When I'm down at the store do you want me to pick up anything else to wear?" Steve asked -- partly hopefully, and partly with some dread in his voice.

"No. I don't think so. I enjoy you wearing the panties and I'm assuming you do as well. I think they've added a lot to our play, but I think when we do this, I just want it to be me and you and not make it about that." Amie responded. "If you want to continue to wear sexy underwear -- and I hope you do -- you can do so, but this is about a new start for us.

The next day, Steve took his lunch time and headed over to the store. He saw the shopkeeper and asked her for the box she was holding for Amie. The shopkeeper looked him in the eye, and then disappeared in the back for a moment, emerging with a non-descript black paper bag. Steve went to pay, but she told him Amie had paid for it earlier in the week. He shook his head at this -- she knew where this was going long before he did...

When he got home, Steve opened the bag and the box and found 3 black silicone plugs arranged in the box in ascending order. The box indicated this was a "trainer kit" and he was thankful that Amie hadn't gone with something extreme. Following the shopkeeper's instructions, he washed all of them in soapy water and set them aside. He texted Amie (even though she was just down the hall, but he could here her on a videoconference call) and let her know he had made his run, and then got back to work. Amie popped her head in the door of his home office and let him know she had ordered delivery, and told him when he was done to meet her in the bedroom. Steve felt his cage tighten a little bit, and he adjusted things, then shut down his system and headed off to the bedroom.

Amie greeted him "Okay, so we've never played with anal before, but from what I read we want you to clean up. So, I need you to go use the bathroom, and then take a quick shower to clean-up.

Steve complied and came out of the shower and toweled off to find Amie standing in the middle of the bedroom wearing rubber gloves, with the smallest plug in her left hand and the lube in her right hand.

"All good hon?" she asked, and when Steve nodded, she continued "So we're going to try the smallest plug to get started. From what I read, we're going to slowly put this in you and then let you get used to it. We'll put it in for dinner, and then you can take it out and then we'll try it again later before bed."

Steve nodded, and then at Amie's direction, he put his hands on the bed and spread his legs. He thought she was going to go right for it, and was surprised when she started rubbing her hand up and down the inside of his things, and then massaging his buttocks. He let out a deep breath and relaxed. He then felt her repeat the gentle massage, but this time with the anal plug in her hand. After he relaxed a little more, he heard the click as Amie popped the top on the lube. Amie stopped to put a hand towel on the floor between his legs, and then he felt her dribble the lube on his behind, and start to rub the lube into his crack. She had him spread his legs even wider, and asked him to bend over further and put his chest onto the bed. Amie complemented him on his behind, and then he felt her work a finger around his rosebud. A few seconds later, he felt the plug pushing gently against his sphincter. Amie didn't try to force it in, and he could feel her turning it clockwise then counterclockwise, putting a little pressure against the opening.

"Push out a little like you're trying to go to the bathroom" she instructed. He did so, feeling the pressure of the plug against his opening. On his third push, he felt it moving slowly into his anus, hurting as the wide part pushed past the opening, until finally it was seated. Amie let him get used to it, and then removed it. She asked him once again to push out, and this time the plug slid in much easier.