Is Something The Matter? Ch. 07

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Hey All – This is the conclusion to the story of Steve and Amie and their experience with Chastity Play. I concluded it… but hopefully left it open for some sequels. If you haven’t read the first 6 parts, you probably should, or else you’re going to be quite confused.

As a reminder, this story has elements of male chastity, female-led-relationships, cross-dressing, feminization, CBT. If those things aren’t your bag, please move on.

All elements depicted in this story that involve BDSM represent, safe, sane, sober and consensual play. If you’re going to mess around with these things, please do so in a safe manner, and always get consent!

Hope you all enjoy and thanks for the comments, messages, and reviews.


“Is Something The Matter?” Steve wondered. He was standing in the ensuite bathroom in their bedroom, one foot up on the toilet, the other on the floor as he tried to fit the next larger size anal plug into his anus. His sphincter wasn’t giving in and it was PAINFUL. He was using plenty of lube, but he just couldn’t do it. He dropped his leg, and stood staring in the mirror. Staring back at himself, he saw his naked body – hair shaved from his armpits, chest and stomach, upper thighs and around his caged penis. He took a deep breath, and willed himself to relax. This was something he had asked for, and he didn’t want to call Amie into the bathroom to ask her to help him insert the anal plug.

Steve heard a soft tapping on the door, and Amie’s muffled voice “You okay in there?” she asked.

Steve let out a long breath. “I’m having a little trouble with the next size up.”

He saw the doorknob turning in the mirror, and slumped his shoulders in defeat.

Steve continued “I don’t understand WHY this is happening, its like my body is just closed.”

Amie stood behind him and to the side and put her hand gently on his shoulder, and looked at him in the eyes through the mirror. Your problem is… you’re too tense. I can feel it in your shoulder blades. How about you exercise or do some yoga or maybe take a hot shower to relax.

Steve snapped back “I can’t. I have to get on a client call. I just don’t have time to do this Amie.”

“Hey. That’s enough.” Amie moved over to the toilet, put down the lid and sat down. She pointed to her lap “You know better than to talk to me like that, so get over here.”

Steve dropped his head, walked over and arranged himself over her lap. Amie tapped his legs to spread them apart, and Steve found himself staring at the tile on the floor of the bathroom.

“You’ve made a lot of progress these last few months, and I understand you’re under pressure at work, but taking that tone with the woman who has given you the last 2 months of attention and care is not acceptable.”

With that, Amie started spanking Steve’s behind, alternating between cheeks, and landing a few blows on the top of his legs. True to his training, Steve was counting along. When they reached 30, she stopped. “These meetings you have today – I’m assuming you’ll be sitting in front of your computer?”

“Yes Miss” Steve replied.

Amie reached behind her and found her wooden handled hairbrush sitting on the back of the toilet tank. She lay it on Steve’s behind so he knew what was coming, and then said “Well, then I hope you’re good at hiding your pain, because you’re going to remember this throughout your call. What is your safe word?”

“Banana” Steve replied.

After getting that acknowledgement, Amie proceeded to give him an additional 16 swats with the back of the hairbrush. After the first few she saw the color rising in his behind, and she heard him shout out in pain. Once she had finished, she softly rubbed the cheeks, hearing him whimpering and feeling his body relax. “There” she thought to herself, “much faster than a yoga workout”. She ordered Steve to stand up, and then place his hands on the sink. He thought she was going to continue her assault, but instead felt the cold lubricant being worked into his crack, and then the plug pushing once again against his sphincter. With a few moments of nudging, Amie instructed him to push-out, and the larger plug was seated.

Amie caught his eyes once again in the mirror. “I don’t expect to have to do this ever again. But if you continue to speak to me like this, be assured that when I do peg that little ass of yours, it will be in this room, not the bedroom, and you will watch yourself in the mirror as I take the last vestige of your manhood. And you know, if we do have to go this direction, I don’t see the need to unlock that pathetic little cock. Do you understand?”

Steve was shocked by the terse manner of Amie’s statement. This was NOT how they had pictured it, and he did not want her to put off the end of Locktober in any sense of the word. He quickly nodded and said “I understand.”

“Good. Now clean yourself up and get to work” Amie concluded. Amie washed her hands thoroughly, then dropped the hand göztepe escort towel on the floor and stalked off to her office. She had to get out before he saw her shaking. Her reaction to Steve’s insubordination had shocked her as much as it had shocked him, and she needed some time to cool off.

An hour later, Amie emerged from her office. She heard Steve on a Zoom call, and peeked into the room. He had his laptop up on a Sheraton bureau and was standing in front of it. She waited for a moment of silence, cleared her throat, and pointed at his chair. Steve nodded, then turned off his camera briefly, replaced the laptop on his desk and sat down quite gingerly on the chair. He turned on his video feed once again, and looked to Amie for approval. Seeing her nod, he continued with her meeting.

Amie knew he had the double-whammy of sitting on a raw bottom, and doing so while having a plug in his ass. She shook her head, wondering if they finally gone too far. On the way back from the kitchen, she looked in on him again, watching him continue to try to make himself comfortable, and then headed back to her office.

After his two morning meetings, Steve shot off like a cannon to get to the bathroom to remove the plug and also use the bathroom. He cleaned up, and set the plug on the countertop next to the bottle of lube. He would put it in again in the early afternoon. Hopefully this time would be a little easier if he remembered to relax and push-out against the intruder. He looked down at his caged cock, noticing that there was about 1/2″ of space between the tip of his cock and the end of the cage. Oh my God, he thought – it really is happening. No. That can’t be. He tried to will his cock to get hard, but in his panicked state, nothing happened. He tried thinking about porn, he tried thinking about Amie… nothing. Oh God, he thought – its shrinking and I can’t get hard.

Steve started to perspire. There he was, standing in the bathroom, his pants around his ankles, his cock in a small cage that was now too big for him, his balls literally aching for the release they hadn’t had since the beginning of September. This was a full panic attack. He pulled up his pants and darted over to Amie’s office. She was on the phone when he entered, but seeing the look of panic in his eye, she asked the person on the other line to hold, and muted the phone.

“What’s going on? What’s the matter?” she asked.

“I just. I’m having a lot of emotions here” Steve stammered. He tried to articulate his fears, but couldn’t put words to them.

“Come over here, and kneel next to my chair. You’ll need to be quiet.” Amie unmuted the phone, and Steve settled down next to her. She began lightly rubbing his shoulders and back as she spoke on the phone.

Steve could hear her on the phone – she was now using the same authoritative voice she had with him earlier. He immediately started to relax – both from the proximity to her, and by soaking up the strong commanding presence she had.

Amie completed the call, and looking down at him said “You can stay here as long as you like, but I have some more calls to make.”

Steve nodded, not moving a muscle. He heard Amie get on with her boss and report on her last call with opposing counsel. Finally, he felt relaxed. He stood and left the room. He stopped in the hall, opened his pants and found that his cock had once again filled out the end of the cage. He breathed a sigh of relief. He reached down and felt his balls – noting how full they were, and then headed back to his office to work through his afternoon. Around 4PM, Steve found himself on a Webinar – which was a review for him. He left the webinar running, and then snuck back to the bathroom. He prepared himself and got the plug. As he was looking at it, he got an idea, and decided to try the largest of the 3 plugs – just so see if he could do it. After finding it, doing some breathing exercises, he inserted the largest plug. Steve was surprised to feel it going in so easily. He removed it, twisted the end a bit to tease his sphincter and then re-inserted it. Satisfied with himself, he pulled up his pants and returned to his office.

When Steve went to sit down, he realized that the larger size – while it wasn’t wider – was definitely longer, and a dull throb went into the pit of his stomach, his eyes bugging out. He took a couple of breaths, and tried to concentrate on his computer screen.

Around 6:00, Steve wrapped it up for the day. It was Amie’s turn for dinner, and he could smell the curry that she liked to make every few weeks. He returned to the ensuite and gently removed the plug, then hopped in the shower to freshen up. On exiting the shower, he put on a fresh pair of thong panties, a camisole top under heavy sweatshirt and sweatpants. He liked the feeling of the tight camisole as it clung to his body while the sweatshirt moved independently. He also like the thong panties – which allowed his still halkalı escort sore behind to be a little freer. He thought back to the spanking Amie had given him that morning, regretting the things he had said – not just because of the punishment they had elicited, but because he knew that in his impatience, he had disrespected the person he loved dearly.

Dinner that night was quiet as they caught up on their day. Not a word was spoken about Steve’s mini-breakdown that afternoon, or Amie’s spanking earlier in the morning, until Steve stood up to clear the dishes. Amie noticed the whale-tail of the thong and the lace trim of the camisole as he walked away. She shook her head and left him to be. Amie returned to her office, pulled up an anonymous browser session and ordered some of the items she had looked at the night before. Latex-look leggings, a boned bustier, and long latex glove. The only thing missing was a pair of long boots, but she wanted to try those on instead of buying online. Just as she was about to hit the ‘check-out’ button, she noticed the tab that said “mens”, and perused. She thought about buying Steve some sexy men’s underwear, but decided she was happy with what they had already gotten. She was interested to see if he stuck with wearing panties and the like after their Locktober play was over. She had introduced the feminine garments to him as part of the play (and quite frankly they weren’t necessary for chastity play, but they both seemed to enjoy it). She looked forward to the day that he woke up with no chastity device in place and decided to put on a sexy thong, and smiled to herself with that thought in mind.

Steve found her in the office just as she was closing up her web browser. “Anything special you want to do tonight?” he asked.

“I’d like to try the largest plug if we can” Amie responded.

“Already ahead of you hon. I wore it this afternoon. Found out that the size wasn’t the issue, it was the length that took some getting used to, especially when I sat down.”

“Well, look at you. Mr. Thong Panties and Large butt plug!” Amie exclaimed. How about we just chill tonight – tomorrow is Saturday and the 31st, so we need to rest up for the grand opening.”

“Grand opening? What store?” Steve replied quizzically.

“Hon, I meant the grand opening of your backside. Remember – at midnight, you lose the cage, and probably 15 minutes later, you’re going to lose your virginity again.” Amie teased.

“Oh. Right. Okay.”

“Speaking of shopping though… I’d like to go get some new boots tomorrow” Amie interjected.

Steve nodded, thinking it was a trip to REI.

The next morning was rainy. Steve stretched, feeling the satiny nighty pull across his body. He knew he needed to shave again – and could feel the stubble on his chest catching on the satin of the nighty. He got up quietly and headed to the guest bathroom so as not to disturb Amie. When he finished in the shower and shaving, he walked back to the bedroom. The door was ajar and he could smell coffee brewing in the kitchen. Steve got dressed – hung up his nighty and grabbed the laundry to take to the basement. Once he had started the first load, he headed up to the kitchen and found Amie still in her robe.

“What took you so long in the shower? If I didn’t know you were locked up, I’d think you were being a naughty little boy” Amie challenged.

“Ha. No. I had to shave, and shaving these days has taken on a whole new dimension” Steve laughed in response.

“Welcome to my world. Before we head out, I’d like you to put in a plug. You decide the length.” Amie responded.

Steve nodded his understanding and went about getting breakfast together and then headed out to the garage for a few minutes. He returned, went up to the bathroom and once again put in the plug – choosing the medium sized one since they’d be driving in the car. When he got downstairs, Amie was waiting for him in a short black skirt, tights, a low-cut top and her black leather jacket.

Steve looked her over and commented “That’s quite an outfit to go get hiking boots, but okay.”

Amie chuckled to himself, grabbed the car keys from the kitchen counter and said “I think I’m going to be just fine.”

Amie took them out on the expressway, and Steve noticed that they had passed the exit for REI. Only then did he put it all together and realize they weren’t getting hiking boots for Amie. At the next exit, she pulled off and into the parking lot of a high-end shoe store.

Amie looked over, waggled her eyelashes at him “Let’s go” she said, rolling the words with her tongue, and just adding to Steve’s excitement. He felt himself getting hard in the cage with the anticipation and with her level of control.

Amie tried on 5 different style of boots, each pair reaching a longer way up her leg, until she settled on a black boot that came halfway up her thighs. The skirt she was wearing actually reached below haramidere escort the top of the boot, so she rolled the top to adjust it up, making it into almost a micro-miniskirt. She wore the boots out of the shop, leading Steve who brought her old shoes in the boot box. Amie popped the trunk so he could stow the box, and then got in the car.

Steve opened the passenger side, and was stunned by the sight before him, Amie’s skirt riding up to her crotch, her panties just visible underneath, and the top of the boots just inches away. She turned to him, and pulled the key out on the necklace to show him “I bet you wish I didn’t have this, right about, now don’t you?”.

Steve had no words. He just sat down and looked ahead, until he turned and caught her eye and they both burst into laughter at the ridiculousness of the situation, and at the reaction of the clerk in the boot store when Amie rolled her skirt to make it shorter.

They ran a few other errands, Amie turning heads on the street and in the mall as she strutted around. She felt 100% in control. Steve on the other hand was starting to get uncomfortable with the plug still in his ass after so long. Amie dipped into a lingerie store -chasing Steve away when he tried to follow her in. This wasn’t Amie’s usual store, as they were in a different part of town, so Steve was thankful that she dismissed him.

Finally, he asked if they could go home, or at least find somewhere where he could safely and discretely remove the plug. Amie reached into her purse and found a Ziploc bag. They found a fast-food restaurant that they knew had “single-style” bathrooms so Steve could get some privacy. He removed the plug, cleaned it up the best he could and stowed it in paper towels inside the Ziploc bag, stuffing the entire bag into an inside pocket of his coat.

When he sat down again in the car, he breathed a sigh of relief, until Amie looked over and asked “Is that butt plug in your pocket, or are you just happy to see me?” They both broke into peals of laughter once again.

They headed back home and Amie had Steve order some delivery – timing it so that it would arrive soon after then did.

Once dinner was cleaned up, Amie told Steve to go get washed up in the spare bedroom. He grabbed a robe and slippers as Amie had told him – in no uncertain terms that she didn’t want him wearing any of his feminine garb tonight. Steve did his best to clean himself up. He had studied how to use an enema bag through the wonderful world of YouTube, so he cleaned himself the best he could, showered, touched up his shaving, and then donned the robe. At YouTube suggestion, he put just a little lube on his backdoor, and then headed down to the basement. Earlier, he had retrieved a large queen-size inflatable mattress from storage in the garage. He now had it fully inflated and fitted with a pair of dark sheets. He stacked hand towels on the table next to it. He sat and waited for Amie.

Finally, he heard her coming down the stairs, so he removed his robe and knelt on the floor. The soft light from the track lighting in the corner and the various candles he had put out throughout the room cast an eerie glow. Steve knelt in position, his eyes on the floor, waiting for Amie to command him.

He heard the unmistakable sound of her new boots clicking and clacking their way across the floor, until she paused behind him. “You may look up.”

Steve raised his head, and turned to see her. The black boots rose from the floor, encasing her perfect legs. Then it was the bare skin of her delectable thighs, followed by a small black lace panty through which he could see her fully shaved pussy. Steve’s heart skipped a beat. Following upwards, she was wearing a purple Merrywidow with a scooped front that split between her breasts. In her right hand was a leather tawse, about 12″ long. She looked down on him with her heavily made-up eyes, her eyelashes extended.

Amie laid the tawse lightly on his shoulders, and then started walking around Steve slowly. “Well, we’ve made it through the month, my dear husband. I didn’t know if you’d make it this far, but I’m so proud of you. Right now, I’m assuming those balls are ready to burst, and I’m ready to help you get rid of that pain… that blockage is perhaps the better word? But first we have some business to attend.”

Steve nodded his understanding.

Amie reached down with the tawse to gently lift the cock cage for inspection. Steve’s cage lifted ever so briefly and then dropped down again, causing him just a little bit of a grunt of pain as it pushed down on his very full balls. She then proceeded across the room and sat down on a high back dining room chair, resting on the chair arms, and crossing her legs so Steve’s vision from the floor was centered on the long black boots that covered her legs. Amie sat there for just a moment, then instructed him to crawl across the floor. She cast a pillow down on the floor for him to kneel on, and when he arrived she slowly and deliberately uncrossed her legs, spreading them wide so he could see that the panty she wore was crotchless.

Steve stared directly between her legs, wishing he could dive in to those delectable folds. He smelled the sweet scent of lavender – the skin crème Amie used – and started salivating.

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