Is Something The Matter? Ch. 05

If you haven't read Chaps 1-4, this might not make a whole lot of sense. I'm trying to wrap this story up, but it keeps telling itself.

This story has FemDom, Bondage, Chastity, Strap-on Play, Cross Dressing, Gender Play etc etc. If you aren't into any of that, please find another story.

Thanks to all for your comments, suggestions. Sorry it took so long to get this one out there - I had a major case of writers block. This is Part 5 of what was supposed to be a 2 part story and if you read through this one, you'll find that there's definitely the need for a Part 6.

Chapter 5

"Is There Something The Matter?" Amie asked this question to herself, considered it again, and decided that nothing was the matter. Things were DIFFERENT than they were a year ago at this time. A year ago, at this time, she and Steve were getting their costumes together for big Halloween parties. This year - the year of the "VID" they were avoiding other people, and Amie was getting Steve mentally ready for the end of Locktober, when she would finally remove the chastity device, she had placed on him at the beginning of the month.

After a reset at the midpoint of October, Amie had recommitted herself to the concept of teasing Steve each day. She had dug into the Halloween bin and pulled out some fishnet stockings which at one point had been part of a 'sexy gangster' costume. Or was it 'sexy flight attendant'? She couldn't recall. But right now, as she lay in bed propped up on her pillows, she could see her old costume's fishnet stockings with the top of Steve's head in the middle as he enthusiastically worked to bring her off with his tongue and fingers. He had actually gotten quite good at this, and Amie definitely didn't want to go back to the way things were, when he would go down on her for like 2 minutes, and then sit back and wait for her to just absolutely gush about what a great job he did (he didn't) and how she had cum like a porn star (she hadn't), and how much she was looking to return the favor (she wasn't).

It was October 27th. Just four days until what Amie called 'D Day' - the day she planned on unlocking Steve and also changing their relationship forever. She had started planning this in September, and she had slowly conditioned Steve to be ready for the next step of her control. Everything started with the tease and denial of chastity. It progressed to adding some Pavlovian elements through the use of scent (a lavender smelling skin crème of which touched up a little every time she wanted to tease Steve or initiate some sort of sex with him), touch (she had replaced his boring boxers with various panties, and his nasty sleep shirt with a camisole), taste (she had gotten Steve in the habit of going down on her after each time he penetrated her with their strap-on (necessitated by the fact that he was locked up), and sound (Amie had initiated the conversation about a week ago about what it feels like for a woman to let a man inside her, and had slowly built that conversation up to the point where she hoped Steve would willingly and graciously accept that his first orgasm AFTER he was released from chastity would come from Amie pegging him with the strap on).

Amie thought back to that last bit, as she felt Steve insert a finger in search of her G-Spot, and she shuddered just a bit - he WAS getting good at this. The conversation with Steve had flowed easily. They had reviewed old loves, and old sex partners with one another. Amie had told Steve previously of when she lost her virginity in high school, but now she expanded on that and told him what a dreadful experience that had been (in hindsight of course - at the time, she thought she was the belle of the ball). The cocky soccer star who had first bedded her (can you call rubbing her back raw on the rug in the family TV room, while some 18-year-old focused on achieving his own orgasm, and calling it "doing it") be considered bedding? In retrospect not. Amie explained to Steve that the first time she had really enjoyed sex was in her sophomore year of college when she had made not just a physical, but an emotional connection with the grad student who served as her college RA. The relationship started as a hookup, and then a booty call with more frequency, but Amie had - one night - completely committed herself to the sex she was having, and fully appreciated the intimacy and vulnerability of letting another human being into her body. That was the night that Amie understood what sex really was - and that first time she had been so emotionally overwrought by the act that she actually cried after she came. They were tears of joy, sadness, and relief all at once as she finally understood what sex was supposed to be about.

Unfortunately for her, Jorge (her RA) thought they were something different, and while that had been the beginning of Amie having an emotional connection to one person through sex - it was also the beginning of Jorge pulling away from her, and leaving at the end of that Spring Semester to do his graduate research overseas.

Amie shook her head to expunge Jorge from her bedroom, and concentrated instead on the fact that Steve had simultaneously found her G-spot and her clitoris, and she was in for a ride. She started to spiral up toward her climax, akin to being caught in the updraft of a tornado. She reached down to steady herself by grabbing Steve's head. As she looked down, she could see his ass in the air, the red ruffle panties he was wearing were visible behind his mane of hair, and she felt her body just freeze with the beginning of the orgasm - what the French called 'le petit mort' - or "the little death". Steve felt her reach her orgasm, and adjusted his technique to keep her surfing on the crest. Finally, Amie came back to Earth and felt Steve begin to kiss his way back up to her, finally resting in the crook of her arm.

Steve was out of breath - Amie had clenched her thighs there at the end and between that and her pushing his face deeper into her pussy he needed some time to recover. It had been an interesting evening (to say the least). Amie had texted him to join her in her home office around 4PM. He found her on a WebEx. She explained that her sound was muted but her video was on, and asked him to get her a glass of wine, and then help her out under the desk. He knew what that meant - quickly moved to get her a glass of white wine in water glass (to hide the fact she was drinking while on a work call) bring it back to her, and then crawled under the desk to find that Amie was wearing a pair of fishnet stockings under her short skirt. Wow! The cage got tighter as he reveled in how sexy Amie had become. The skirt had been hiked up; Amie was sitting at the edge of the chair. Steve adjusted to the small confines under her desk, and was surrounded by the scent of lavender. He wiped just a bit of drool from the corner of his mouth and started kissing his way up the fishnet stockings until he reached his prize.

It wasn't long that he was down there when he heard Amie speaking - she was wrapping up her participation in the video call and shutting down. He heard her colleagues say goodbye, and then silence as she had closed the screen. Amie leaned back and enjoyed the attention, and Steve heard the sound of her desk drawer opening and closing, and then a click and a buzz. In a moment, Steve's position between her legs was joined by a buzzing cock-shaped vibrator. He sat back to watch her work the vibe over her clit, and up and down her beautiful pussy lips, but soon felt her hand pushing him back into the fray as he and the vibrator competed for space in that heavenly area.

Amie let Steve continue for a while, and then changed the angle so she could slowly fuck herself with the vibrator, while Steve concentrated on lapping up the juices that escaped her. She then removed the vibrator, turned it off and told Steve "be a dear and clean it off". Steve hesitated and then changed to licking the vibrator. Amie continued "No. I need you to really clean it" and proceeded to push the tip of the vibrator into his mouth, slowly pushing the length deeper into his mouth. Unused to the intrusion in his mouth Steve did his best, but soon felt Amie remove the vibrator and push back her chair.

She looked at him, kneeling beneath her desk as she adjusted her skirt back down. "The good news is apparently you've never sucked a cock before. Let's get dinner and then we can clean up and do our daily cage inspection."

Steve and Amie worked in the kitchen in tandem. They both had their specialties, and soon they were sitting down to a tasty dinner. When they finally pushed back from the table, Amie said "I'll take care of dishes - you go get cleaned up and meet me downstairs.

Steve hit the shower and used the spray attachment to make sure his cage was squeaky clean. He also touched up shaving. Amie had asked him to shave his chest and armpit hair a few weeks back, and he was getting used to the feel of not having so much body hair. He also touched up his beard area to finish the look, and then headed into the bedroom. He figured he'd be naked again tonight, so he grabbed his robe, but then thought again and went back to his underwear drawer and found the red ruffled panties. He had bought them at Amie's suggestion but hadn't had a chance to wear them yet, so he thought he'd surprise her. They were probably the most 'girly' panty he had and not something he could normally wear under a pair of pants. After he put them on, he checked himself out in the full-length mirror - and admired how they made his ass look, as well as how they covered his caged cock in the front. He made a mental note to shave the top of his things a little better just to improve the look, and then gently ran his hand across the ruffle in the rear of the panty, feeling the slight movement and getting a bit more excited. When Amie had introduced him to wearing panties, he had felt uncomfortable with the idea at first, but now he was looking forward to seeing how the material felt when he wasn't caged in November.

Steve made his way downstairs, finding the kitchen empty, and saw the door to the basement open with some light peeking out into the hallway. This meant Amie was already waiting for him. It had now been almost 2 months since he had cum, and he was getting desperate. The littlest things set him off - from the smell of Amie's body lotion, to the sight of her gorgeous feet in a pair of slip-ons, to the soft swish between the robe and the ruffled panties he was wearing for the first time. As he made his way down the stairs, he saw Amie over by the armoire where they kept the toys, her back to him.

"Have a seat. The cuffs are on the bench, we're going to do an inspection tonight" Amie announced.

Steve made his way over to the weight bench that had become their defacto bondage bench. They had discussed getting a different piece of equipment - or several different pieces of equipment - and Steve had reached out to some Etsy stores that sold things ranging from horses to St Andrews' Crosses, to something he had just discovered called a CBT chair. He was hoping that he got some additional commission in October and November so he could get them ordered for Christmas delivery. Sure enough Amie had left out the ankle and wrist cuffs, and Steve put them on, attaching all but one arm to the weight bench. He looked up and noticed that Amie had made her way over. She was still wearing the skirt and the fishnets from earlier today, but the blouse was open another button and he could tell that her bra was missing, and he felt the cage get tighter. There was something different as well about the way in which she was standing and moving around, but he couldn't quite figure it out. The only clue was the devilish look on her face.

"Well look at you. Red Ruffle panties - aren't you cute as a button" Amie asked.

Steve gulped, hearing that and blushing a bit in embarrassment. He hadn't been called 'cute' since he was six. Amie continued, "If I had known you were wearing those, I would have had you give me a show before we strapped you down. Still, I think we're going to get those out of the way and keep them fresh for later."

She had Steve scoot forward on the bench and lift himself up so she could pull the panties down his legs, and then one-by-one, she removed his ankle shackles to remove the panties from the picture. Once she had them completely removed, she held them up in front of her face to admire them, commenting on the ruffles, and the big red bow in the back "It's like a bow on a gift for me to unwrap! I think you should wear these to bed tonight, but then again, maybe not, because I'm going to be grabbing your ass all night!"

Steve didn't think he could blush any redder, but he did. He shifted slightly in his seat, a little disconcerted by the thought that a year ago, before he had started the chastity play, HE was the one who would be grabbing Amie's ass all night.

Amie announced that it was an "inspection night" meaning she was going to remove his cage to make sure everything was okay, and there weren't any sores forming. Sometimes Amie would use this opportunity to inflict a little pain as well, and as Steve winced thinking about that, Amie consoled him "Don't worry hon. You've been such a good boy this month that we don't need to do that. We are going to run a little experiment, however." She looked up from unlocking him and caught his eye.

Steve caught that look - knowing from experience that whatever was to happen that night had long been planned (and likely replanned) by Amie. He was thankful that she had adapted to this role in the relationship. As she stood up with his cage and walked away, he noticed once again that she was walking differently - but couldn't figure out exactly what was different. After Amie put the cage in a bowl of soapy water to clean it, she returned with a bottle of lube in one hand.

"After we make sure your little guy is still healthy, we're going to edge. I picked a card at random from the card deck and came up with an '8', so its 8 edges tonight before you're locked back up."

Eight edges? Steve knew that Amie's edges were an exquisite torture that he both anticipated and dreaded. She used her hands - and sometimes her mouth - to bring him just to the edge of an orgasm, and then leave him there for what was likely a few minutes. To do this 8 times when he hadn't come in almost 2 months was going to be almost too much to bear.

"We're also going to do a little experiment tonight, and if you're really good - we might cut down the number of edges - or we might add one or two. That's going to be up to you. Now remember, you still have a safeword. Please repeat it to me" Amie asked.

"Banana" was Steve's automatic response. They had been using that safeword for 3 months and he had only used it once early-on. Since then, his ability to withstand everything Amie had dished out had evolved, as had her ability to sense what he could and could not take. She knew she had almost pushed him beyond the limit back at the end of September when they did a ballbusting session. Steve had gone into subspace that night, and she was almost afraid that he was so deep into it, that he forgot he had a safeword.

"Okay" she said, pulling up a chair, she put on a rubber glove and covered it with lube. Amie inspected his cock - particularly the head, and then lifted his balls to check to make sure that the ring wasn't causing any rubbing below his testicles. She noted that his cock needed a shaving, but determined to let things be until after Locktober was over. She looked up and saw his shaved chest, rubbed her ungloved hand over it, noticing that he must have just shaved again this evening, as everything was smooth. "Everything looks good. You're becoming a chastity pro, hon. I think when we DO let you out of this chastity cage, you're going to beg to go right back in"

Steve couldn't believe that. He enjoyed being in chastity, but he was so looking forward to being free to do things like stand while he went to the bathroom, or just adjust himself when he was sitting wrong in a chair... All those things he had unknowingly given up when he and Amie first started playing with long-term chastity. He felt himself getting hard - as Amie's gloved hand went up and down his shaft, pausing here and there to caress his balls, or to just tease the head. He could feel the orgasm rising as Amie teased him with light touches.

Amie saw Steve's testicles pulling inward to his body and knew that it was soon time to stop and leave Steve at the edge, and just at the last moment, she stopped, and sat back. She watched his cock move of its own volition, trying to simulate the touch it craved but finding nothing but air.

Amie waited a few minutes until Steve calmed down. She saw his testicles drop once again, and his erection flagged to half-mast. She leaned forward, making sure to give him a peek down her blouse and started again. She continued the technique, saying little to Steve as she concentrated on getting him once again to the edge. After a few minutes, the telltale signs were there again, and she stopped. This time, it took him longer to relax, so she got up and went over to check on his cage. She pulled the pieces out of the soapy water, wiped them off with a soft towel and laid them aside to dry.

Amie then returned, and put fresh rubber gloves on (this time on both hands) and started taking Steve to his third edge of the evening. Again, it took half as long to get him to the edge, and twice as long for him to relax. As she began the fourth edging, she scooted forward on the chair so Steve could see the lacing tops of her stockings as her skirt rose. She saw Steve focused like a laser on her legs, and used one hand to lift his chin so he was looking at her.

"This is number 4. There are 4 more edgings, but I'm going to give you a chance to alter that in a few minutes. Remember though... nothing is free."

Amie resumed her attention to Steve's cock and balls, this time moving at half the speed to really draw out her sensual caresses. Steve was ascending to orgasm, his eyes rolling back in ecstasy when Amie stopped suddenly. "Okay, so you're completely hard now, and its time to check something out." Amie stood up, lifted her short skirt and revealed that she was wearing the strap-on with the medium-sized dildo attached.

Revelation of why Amie had been walking oddly a few minutes back hit Steve like a freight train. Then it hit him - she was wearing the strap-on! That was NOT something they had done or talked about in the past.

Amie reached down and lifted the fake dildo so it rested in her hand. She then stepped forward and lined it up next to Steve's erect member. "Just as I thought, you're hard, but I think all this time locked away has caused your little guy to get... Well... Smaller!"

Steve felt the blood rush to his face once again as he tried to mentally WILL his cock to grow. Amie saw him straining and laughed out loud. "Sorry hon, I know you're smart, but I don't think you have the ability to will your little cock to be harder. Although I'm sure over the past month you've gotten good at willing it not to get hard in the cage."

Steve gulped, realizing the futility of the act, and then looked up at Amie. She stood there totally empowered - looking down at him with a grin. "So earlier when I had you clean the vibrator, I realized you'd never ever played with another cock. If we really want to break down the barriers in our relationship, I want you to know what sex is like for me - in all ways to bring us closer together. Tonight, I'm going to trade you 2 edges for you to go down on this strap on. Sound like a deal? "

Steve continued to look at Amie - as she stood there, one hand lightly stroking the strap on just inches from his face, the other hand resting on her hip in anticipation. He was tempted by her offer - thinking of the exquisite frustration of the edgings he still had to receive, and how he'd likely wake up tonight with a raging hardon confined in his cage, but he still couldn't bring himself to do it.