The next morning after my transgression and subsequent punishment, Fiona sat on a stool at the small bar that separated the main part of the living area from the kitchen and watched me make breakfast. I was wearing nothing except a plain black apron, which I was allowed only while cooking so I didn’t get burned. My exposed bare ass was still covered in angry red welts from the cane. I could say they looked worse than they felt, but I’m not sure that was true.
I stifled a yawn between turning the sausage patties.
The shiny steel cage that was now locked over my manhood had woken me up several times whenever I got an erection during the night. I didn’t realize how many nocturnal erections I had until I was locked up like that. The plug in my ass, which was attached by a bar to the base ring of the cage, was also larger and a different style than the previous plug I had worn and my anal muscles were still adjusting to the new size and shape. I kept squirming to try and make it feel more comfortable since I was cooking and didn’t want to befoul my hands trying to adjust it. I’m sure my wiggling ass was putting on quite a show for my girlfriend, but it was very tight and the bar made it tug on my hole with every little movement.
Fiona seemed to have something on her mind all morning. I assumed she was still upset with me for cumming without permission and trying to hide it from her.
“I owe you an apology,” Fiona said, breaking the silence and surprising me with her serious tone.
“I am the one who should still be apologizing to you,” I said, turning to face her.
“No, you have been punished for breaking our rule so that is done. But I let my emotions get the better of me,” she said, but then there was a gleam in her eye as she continued, “Or maybe it was just the heat of the moment and how much I enjoyed punishing you.”
“What do you mean?” I asked, stepping up to the bar across from her “I have always liked how passionate you are, especially in The Room.”
“Maybe, but I should never have left you alone like that, chained to the wall and in such a state,” she said looking down at her hands on the countertop, “I have always told you that my number one job is to keep things safe and sane.”
That had been her mantra since we first started down this path. It was one of the many reasons that I trusted her, without question. She had been pushing my boundaries in small (and sometimes large) steps over the past few years and built that layer of confidence.
“Not only did I leave you alone for far too long, but I didn’t take care of you properly afterward. So, I hope you will forgive me. I won’t let that happen again. If I do, I expect you to call me on it. Agreed?”, she asked, looking me in the eyes.
“Oh, Fiona, it was nothing I didn’t deserve. Everything turned out fine, no harm done,” I said cupping my hands over hers.
“You deserved the spanking and I had been looking for a good excuse to give your ass a proper fucking”, she said smiling a little.
The reminder made me more aware of the plug nagging at my sore hole.
“Yes,” I said smiling back, “and as humiliating as it was to have three of my own friends use me like that — and I still don’t know which ones…” I trailed off. It made me blush every time I thought about it.
“Just promise that you will speak up if I ever leave you hanging like that again,” she smiled again, “pun intended this time”.
“I promise,” I said and remembered the sausage cooking behind me. I quickly turned my striped bottom back to her gaze so I could finish making breakfast.
Over the next few weeks, the chastity cage turned out to be more of a problem than a punishment. It definitely kept me from masturbating and curbed my erections, but it wasn’t as secure as all the stories and stuff would have you believe. She ordered a few different styles with different ring sizes and cage sizes, but I was still slipping out when I was at my smallest, and most of them would pinch or chafe. She tried steel ones and plastic ones and even one of the new 3D-printed ones. We followed all of the measuring instructions on the different sites, but none of them seemed to work as advertised.
We ended up with two models that I could wear for about a week before they started to rub me raw, usually at the base of my scrotum at the perineum. I was keeping them lubed with a good quality lotion and that seemed to help a lot, but she still had to release me for a few days to let me heal.
Fiona had some conversations with people online who claimed to be long-term wearers of chastity devices and even customer support on one of the better-quality sites that she had ordered from. Like most things on the internet, a lot of them were just faking it, but there were a few who seemed to be genuine. She talked to both wearers and key holders. It seemed the only way to truly secure a penis in a chastity cage long-term was with a piercing, but neither of us was ready for that (well, Fiona seemed tempted). Without that, it very much depended on the shape of the pubic area and the scrotum. Also, “growers” like me (where the penis shrinks down to a very small size when not aroused) were much harder to keep in a cage because they would often get small enough to slip out – exactly my problem. While it was true that the denial and Fiona’s teasing tended to keep the cage quite full most of the time, it is just simple biology that a man can’t stay erect 24/7.
Several people, including customer support, suggested using a strap or belt attached to the base ring that would fit securely around my waist. We started simple and used a bit of thin paracord that we had lying around to make a strap that I could just tie off on one side. That did the trick! I was able to remain in the cage for over a month without issue before she decided that was good enough. The strap kept the ring pulled right against my body so I didn’t slip out when I got small and the cage didn’t move around as much and create a sore. The paracord was kinda ugly though. It looked like I was wearing some kind of rustic bikini.
The cage that seemed to work the best was the black 3D-printed model. It was light, which meant it didn’t pull as much when I was active, like playing basketball or working out with my friends. It was also one of the smaller cages and, because it had been custom-made to fit the measurements we sent them, it was the best fitting for both my scrotum diameter and my penis size. From my normal at-rest state, it fit me like a glove. Even the smallest erection would have my cock trying to squeeze through the gaps in the sides of the cage. It also had an option for a urethra plug but she didn’t want to use that long-term for fear of infection.
This cage did not have a plug attached so I was back to wearing my old ones. That day it was a princess style with a green gemstone. Fiona liked to say it matched her eyes.
“You are going to need a good leather strap now that we have figured this out,” she said one evening while examining my cage to make sure I was staying clean and not having any chafing.
“Maybe we could get a couple of dog collars and do something with those,” I said, thinking out loud.
We had made a few toys in the past from other things and she had several dog collars in The Room that she liked to use on occasion.
“No, I want something nice since everyone will be able to see it,” she said smiling, knowing that I was still quite embarrassed about being kept naked all the time, even (especially) when friends or family would visit.
“I can check online to see if anyone makes something like that,” I offered.
“Actually, I have already talked to a friend of mine who does leather work,” she said, “He is retired but he still makes belts and holsters and such for the general public. He also does custom fetish stuff on the side.”
“Oh, is this your Dom friend?” I asked, almost afraid of the answer. This guy had always seemed scary for some reason.
“Yes, that’s him, Carson,” she said, “He is looking forward to meeting you.”
Fiona had talked about Carson many times. He was an old friend and kind of a BDSM mentor for her. From what she had told me, he was an older guy and had been doing the kinky stuff for a long time. I had never met him and Fiona always spoke with a kind of reverence about him so this felt like I was going to be meeting the Godfather or something.
“Okay, so I’ll get the tape measure and we can send him the measurements and then pick it up, right?” I said hopefully.
“No, silly, he will need to take the measurements himself,” she explained, “and he’ll make sure everything fits properly when it’s done.”
I wasn’t sure why a simple leather strap would need to be so precise but this seemed like it had already been decided. When I didn’t say anything she continued.
“We are going to have dinner with him and his wife, Brandy, this evening, so you will need a quick shower and some clothes,” she said. “Just some track pants and a polo should be fine.”
I knew I didn’t get a say in the matter so I trotted off to the bathroom. I had already showered once this morning and Fiona hadn’t given me any special instructions so I just did a quick one to freshen up. After drying off I hung up my towel in the bathroom and walked to the bedroom. Sometimes I remembered the days when I would have wrapped the towel around my waist before wandering around the apartment, but Fiona had cut that out long ago.
Standing in front of the dresser mirror, I brushed my hair, put on some deodorant and cologne, and then rubbed some lotion around my cage. I pulled a pair of dark blue track pants and a yellow polo shirt out of the drawers and slipped them on. I checked myself one more time. It was strange to see myself in clothes and I was very aware of how they rubbed against my skin. It wasn’t as if I never wore clothes anymore. I wore clothes when Fiona and I went out together and when I went out with my friends, but it was becoming more and more “normal” for me to be naked. Even when we went to her friend’s place, they were more than happy to “allow” me to undress. Even my sister insisted that I strip now, when I visited her house, whether Fiona was with me or not. I’m sure if Fiona could have arranged it I would have been a full-time nudist. Maybe that was coming.
I quit contemplating and returned to the living room. Fiona was on her phone so I puttered around in the kitchen listening to her side of the conversation.
“Are you sure there won’t be any problem with it?” I heard her say.
“Yes, you’re right, I think it would be a good experience,” she said, glancing at me.
“Okay, sounds good, we will see you soon,” she said and disconnected her call.
“So, change of plans. Take those clothes off. You can just leave them there on the counter until we get back,” she ordered.
She had me well-trained, I had my shirt off before I even thought to question it.
“Wait…until we get back? So, I am….” I said and paused, with my fingers in the waistband of the track pants.
“Yes, you are going naked,” she said matter of factly.
“But I…but….” I stammered.
“But what?” she said with an unconcerned look as if this was nothing out of the ordinary.
“Well, umm, what if someone sees me? One of our neighbors, or….” I was feeling flushed, thinking about walking through the halls of our building wearing nothing but…oh god, what if someone sees me in chastity, what will they think…or the plug in my ass. I wasn’t sure which would be more embarrassing.
“The Rameys already know you are nude at home all the time, If someone else sees you, they see you. Just own it. If they ask questions, let me answer them,” she said, using her dominant voice. She was getting into her zone.
My face felt warm and I still wasn’t moving. I wanted to argue the point but I couldn’t think of any words to say. When she turned on her dominant side, it was like a spell on me.
“Get those pants off and let’s go,” she said, snapping her fingers to get me to focus.
“Yes, ma’am,” I said in a hesitant voice as I pushed the pants down my legs and stepped out of them.
Naked once more, I quickly folded the pants and shirt and left them on the counter then crossed the room to stand next to her.
“Good boy,” she said and smiled approvingly. “You should probably put on some shoes.”
I walked over to the shoe rack we kept by the door and looked at my options.
“Just put on those sandals,” she said, noticing my indecision.
I quickly grabbed the leather sandals from one of the top cubbies. I had been wearing these most of the summer for walking around town or even for light hikes on some of the nearby trails. They were comfortable and having my feet somewhat exposed seemed like the perfect complement to the rest of me right now. I buckled the straps around my ankles as she joined me at the door.
“Give me your wallet in case we get stopped or something and you need some identification,” she said.
I froze again for a moment at the thought of getting stopped by the police. She realized that I hadn’t considered that possibility and she sighed, regretting having mentioned it.
“It will be ok, no one will be able to see much of you inside the car. It’s a warm day so it won’t be unusual for a guy to be shirtless,” she said, reassuringly. “And when was the last time either one of us got pulled over?”
Without answering her, I took my wallet off the shelf above the shoes and handed it to her. She stowed it in her purse and pulled out her keys. She didn’t carry a purse often but then I realized that she was wearing skintight leggings so she didn’t have pockets. The thin stretchy material accentuated her slender toned legs and clearly outlined each beautiful globe of her buttocks. Three-inch heels and a silky emerald green top that buttoned up the front completed the look, and her long red hair was down instead of her usual ponytail. It was sexier than what she would normally wear and my cock had clearly noticed as it was pressing against the cage and making me squirm. The movement caught Fiona’s eye and she spotted my condition right away.
“I think you are liking this idea more than you want to admit,” she teased.
I didn’t like it. I was terrified and mortified (okay, and maybe a tiny bit excited), but I just blushed and looked down at the floor as she opened the door. I had to go out first so she could close and lock the door behind us. Suddenly there I was naked in the hallway staring at the barrier between me and my safe haven.
“Better not dawdle, unless you want to be seen,” she called back to me, making me realize that she was several steps ahead of me already. I hurried to catch up.
We lived on the 3rd floor – the top floor of the building. So it was either the elevator or the stairs. Fiona chose the elevator and pressed the call button. This was an old warehouse that had been converted into apartments. We loved the old rustic wood and raw brick walls and even the antique freight elevator. At least I had up until that moment. It was slow and made a lot of noise and I was sure everyone was going to come and peek out their doors to see who had summoned the annoying beast. I almost tried to cover myself with my hands but Fiona had trained me too well and I resisted the urge.
Finally, the elevator arrived and I let out a sigh of relief that it was empty. The door was one large gate. The bottom half was solid but the top half was a metal lattice. It was a cool feature normally to be able to see out as you passed each floor, but it was going to be a nerve-wracking ride for me this time as it felt like I was going to be on display inside this cage. Fiona raised the gate and stepped inside. I followed and quickly pulled the gate down as she pushed the button to take us to the garage level.
Our car was parked in the garage under the building so that was one small favor. I didn’t have to walk through the lobby or out on the street like this. Living downtown, most people walked or biked wherever they were going and only took their car out if they were heading out of the downtown area so hopefully we wouldn’t run into anyone in the garage.
As we approached the first floor, I started to freak out. A man was waiting for the elevator in the lobby! I stepped back trying to hide behind Fiona but she was too close to the back wall so all I accomplished was drawing more attention to myself. I steeled myself, expecting the elevator to stop but it just kept going. I exhaled the breath I was holding, realizing that he was wanting to go up but we were going down to the garage. The elevator wouldn’t stop for him until it was on its way back up.
I didn’t know the man but I recognized him as another tenant in the building. He nodded and I nodded as acquaintances do, then he kinda did a double take as we reached a point where he was looking down into the elevator. From the expression on his face, he wasn’t quite sure what he had seen.
Finally reaching the garage, I noticed that Fiona was smiling as I raised the elevator gate.
“How did it feel to almost be caught for the first time?” she asked as she stepped out.
“I was scared to death,” I said, closing the gate and allowing the elevator to head back up.
“Is that all?” she said, still smiling and looking down at my lap.
I also looked down but I didn’t really need to. I could feel how tight the cage had become.
“Well, it felt kinda daring too, I guess,” I said, blushing.
“Daring is good,” she said, heading towards our parking spot.
All the tenants had assigned parking spaces. Our relatively new small blue SUV was several rows away. I followed behind Fiona, her heels clicking and echoing off the concrete walls and ceiling of the enclosed space. It was well-lit to make people feel safe but today that just put me even more on edge. My head was on a swivel as I noticed every shadow and listened intently to every sound. Our car was in sight when I heard the loud metallic clamor of the garage door being opened!
The garage door was a slow metal roll-up with an automatic opener that was activated by a key fob given to each tenant when they moved in. That meant someone was about to enter the garage and would be driving right past us! The door was up a ramp that curved in a tight corner so they wouldn’t be able to see us until they reached the bottom.
I sprinted past Fiona across the remaining distance to the car and grabbed the handle on the passenger side (she almost always drove when we went together). It didn’t budge, the door was still locked. I patted my naked thighs as if I might have a key in some nonexistent pocket. Panicking, I turned to Fiona, wide-eyed.
“Now where are those keys,” she said, making a show of digging around in her purse and continuing to walk at a leisurely pace.
The sound of the door stopped and now the sound of a car engine could be heard coming from the top of the ramp. I scrambled for a place to hide but the only place would have been between the car and the wall and there was no room. The spaces were barely big enough for the car to fit so we had to pull forward until we touched the wall.
“Fiona, please!” I begged.
“Oh, here they are,” she said theatrically and pulled them out of her bag…then dropped them on the floor. “Oops.”
The car had made the turn and was coming down the ramp. I froze again like a literal deer in the headlights. I was between two cars so I wasn’t directly visible except as the car passed the spot. Maybe they wouldn’t look between the cars. Maybe if I stood very still, I would just blend in and become invisible.
Fiona took her time bending over to pick up the keys as the car drove slowly by. It didn’t stop. They didn’t roll down their window and shout “naked man”.
Our car beeped and its lights flashed, startling me and making me jump and gasp. I pulled the door handle again and this time it opened. I quickly scrambled into the seat and closed the door. A moment later Fiona joined me on the driver’s side.
“Oh no, there’s a naked man in my car!” she laughed.
“Are you kidding? Oops?” I said, exasperatedly.
That made her laugh even louder.
“Just having a little fun,” she said when she could finally catch her breath.
I gave her a wilting look.
“At least someone seems to have enjoyed it,” she said, reaching over into my lap and petting my engorged caged member.
I jerked in the seat and let out an involuntary moan at her touch, which made her giggle as she pulled her hand away.
“Ready for the next stage of this little adventure?” she asked as she started the car and fastened her seatbelt.
“Do I have a choice?” I asked, pulling my seatbelt across my naked chest and legs to snap it into place. The straps felt cold against my skin.
“Not really. But don’t be like that. Enjoy this! Just relax and let it happen,” she said, using one of her favorite catchphrases.
As Fiona pulled out of the parking spot and headed towards the ramp, I was sullen. I still wasn’t happy having this sprung on me without any warning, but it wasn’t like we hadn’t talked about doing something like this for a long time. We were on our way to see someone I had never met before, someone from Fiona’s past that she respected, so I felt like I needed to make a good impression, but I would be naked from the moment we met. Had that been the plan all along? I had to admit that even with the fear, I was feeling pretty aroused. Maybe if I had been able to masturbate or at least edge a little…
We reached the top of the ramp. The garage door was set to close fairly soon after it was raised to prevent cars that didn’t belong from sneaking in behind a tenant, so we had to stop and activate our keyfob to raise the door again. Sunlight streamed in as the door rose, creating a bright beam that traveled across the hood of the car and moved up to the windshield. My brooding gave way to tension again as I was lit up as if by a spotlight. I flipped down the sun visor and then rattled around in the cubby between the seats until I found both mine and Fiona’s sunglasses. I handed her hers and put mine on.
“See, now no one will be able to recognize you,” she chuckled.
This was one of our little inside jokes that we made whenever we were watching a movie or show and someone “disguised” themselves by putting on a hat or sunglasses, so I had to laugh.
“Yes, I’m in deep cover mode now,” I said in a low voice, playing along with the joke.
The door reached its apex and Fiona pulled out into the alley that ran behind our building, following it down to the street where she paused to check for traffic before turning right. I was now officially NIP as they say on the internet – Nude In Public.
Unconsciously I shrunk down in the seat even though there was no way I could get completely below the window. Fiona glanced over at me and chuckled but didn’t say anything.
It was a Saturday and as Fiona had predicted, it was a beautiful warm day, so there were a lot of people out walking along the streets, shopping or meeting friends or whatever they had to do. None of them seemed to notice that a naked man was driving by them. There was a bit of a tint on the side windows so maybe they couldn’t see me as well as I could see them. Every time we had to stop at an intersection I was sure one of the pedestrians crossing in front of the car was going to scream and point or call a cop to arrest me for indecency, but after several uneventful stops, I was starting to relax a little.
“So, I wonder what constitutes indecency here,” I wondered out loud.
“Oh, I asked Teresa about that and she said that this state is fairly liberal when it comes to nudity,” Fiona explained. “As long as you aren’t being lewd, you are pretty much allowed to be nude anytime anywhere.”
Teresa was a friend of hers from University and she was an attorney. It seemed like Fiona may have been planning for this occasion for a while.
“What constitutes being ‘lewd’?” I asked.
“Well, like you can’t be playing with yourself or exposing yourself in a way that is intended to solicit or insinuate a sexual act,” she said, apparently having asked Teresa for the same clarification.
“Well, I won’t be playing with myself,” I laughed, “but does wearing chastity or a butt plug insinuate anything?”
“She said the law was unclear on that but case law around provocative modes of dress suggested that what you are wearing, in and of itself, should not be a factor in determining lewdness,” she explained. “So for example you can’t say that a woman deserved to be raped because she was wearing a short skirt.”
“But am I ‘wearing’ this cage and plug?” I asked.
“She said the cage almost certainly, the plug maybe, maybe not. She could definitely make the case in court, but it would be up to the officer on the scene whether to write you a ticket or arrest you.”
“Arrest me! So maybe I should take the plug out until we get there?” I asked, getting anxious again and squirming in my seat.
“No, don’t worry. You won’t be getting out of the car until we get to Carson’s house and I don’t think anyone can see your ass inside the car…unless you are planning on mooning everyone?” she laughed.
“Okay, I guess,” I said, still worried.
“At least wait until we get up on the highway before you do,” she continued to joke, “I’m sure the truckers would appreciate it.”
“Ha ha, you know what I meant,” I said. She was good at turning my words around on me like that and I hoped she wasn’t getting any ideas.
We were finally taking the ramp up to the freeway. I realized that I didn’t know where we were going.
“So where is Carson’s place?” I asked.
“Rosewood, so not far,” she replied, glancing in the side mirror as she merged into traffic.
Rosewood was an older suburban community known to be one of the nicer areas, but not as expensive. It had been prime real estate for families getting out of the city years ago but now was mostly older empty nesters. At least that’s what I remembered reading back when Fiona and I were looking for our place.
“Now that we are out of town, why don’t you lean the seat back and relax?” Fiona suggested.
“It’s okay, I’m good,” I said. I was looking out the window but not paying attention to anything in particular.
“No, really, lean the seat back and put your feet up,” she said, a little more demanding.
“Oh!” I said, finally realizing what she was intending. “Are you really going to make me do this?”
“Of course! This is your first time out like this, we have to give you the full experience,” she said, making it sound like we were trying out some new restaurant.
There were plenty of pictures and erotic stories online about women exposing themselves to people while riding in cars on the highway. Not so many about men doing it, but I’m sure it happens.
With a sigh of resignation, I reached down and leaned the seat as far back as it would go. The seatbelt was getting in my way so I decided to risk it and take it off. Of course, this caused the car to start chiming an alert, so I pulled the seatbelt down and underneath me and then snapped it into the buckle.
Finally lying back, thinking that they make this seem so much easier on the internet, I started to put my feet up on the dash as Fiona had requested.
“Don’t put your dirty shoes on the dash, take them off,” Fiona scolded.
“Yes, ma’am,” I said.
Still lying back, I pulled one knee at a time up to my chest, unbuckled my sandals, and let them drop to the floor, then put my feet back up on the dash. This kept my knees bent slightly and splayed open with one against the door and one against the center cubby/armrest. With the seat back, my upper body was stretched out straight. I wasn’t sure what to do with my arms so I put them up with my hands behind my head. Fiona gave me a wolf whistle.
“You look good, stay just like that until we get off the highway,” Fiona said.
“Yes, ma’am,” was all I could think to say.
I decided to just accept this and let it happen, as Fiona would say. I closed my eyes and just lay there. I had just started to relax and get comfortable when a sudden honk startled me.
“Don’t worry, sweetie. You just have an admirer,” Fiona said.
I glanced out the window and there was a delivery van next to us matching our speed. I closed my eyes again and moved my hands to cover my face, trying to pretend that I wasn’t naked and on display.
“I think he likes what he sees, he just gave you a thumbs up,” Fiona said, giving me the play-by-play. “Lift your hips so he can see your chastity better.”
Oh god, really? I thought, but I knew she would be mad if I missed this “opportunity”, so I pushed my hips up above the window. My black cage stood out starkly against my pale skin in the sunlight so it was clearly on display.
“Good boy, he is liking that,” Fiona said, “he’s even taking a picture!”
Mortified, I waited for another minute before I lowered myself back down in the seat. The van pulled away a moment later, apparently satisfied with the show.
“I am going to be some random guy’s post on a porn site later,” I groaned.
“Don’t worry, you are in disguise, remember,” she laughed.
I just groaned in reply.
“And if he even got a good shot, I doubt the picture quality would be good enough for anyone to recognize you,” Fiona said, trying to console me.
I knew she was right and I was trying to be upset about it but I was more turned on than anything else. Fiona always knew how to push my buttons and turn even the most humiliating experience into something fun.
We had a few more vehicles slow down and look and one more that honked their horn before we reached the exit for Rosewood. I had been starting to relax a little and enjoy the ride but I had forgotten about our destination.
“You had probably better put your seat back up now that we are on suburban streets,” Fiona suggested.
I sat up and pulled the handle to bring the seat back up to a sitting position, then jiggled it a little to get it in just the right spot. I didn’t bother with the seatbelt and just left it the way it was.
The houses here were pretty nice. Mostly late 70s and 80s era but had been well built and maintained over the years. They weren’t huge houses but they were built for a decent-sized family and there was a lot of grassy yard separating them as well as a lot of big mature trees and nicely maintained flower gardens. We passed a few people who just seemed to be out for a stroll or walking their dogs. They were all older, maybe 50s or early 60s. There was only one house where we saw a couple of kids playing in the driveway.
Even though no one was paying us much attention again, I continued to get more and more nervous as we went along. I knew at any moment Fiona would turn into one of these driveways and I would be meeting her Dom friend, Carson.
“Don’t worry, baby. You’re going to like Carson and Brandy,” Fiona said, picking up on my mood change.
“Are you sure? This looks like the kind of place where we might get mobbed by the Home Owners Association if they spotted a naked man in the neighborhood,” I said, trying to be funny.
“It will be fine. He has a mostly private area in the back so you won’t be running naked around the block or anything,” she said smiling.
That bit of information only helped a little. My biggest concern was still meeting Carson himself.
A few moments later, Fiona slowed the car in front of a nice ranch-style home with dark red siding and a front porch built with a brownish stone. She turned into the driveway and followed it up to what turned out to be a drive-through carport that allowed her to park behind the house in front of a large garage made from the same stone as the front porch. The garage had a roll-up door on the front and a regular door on the side. A stone path led from the side door to a patio off the back side of the house.
An older man, probably in his late 50s, was sitting in a chair on the patio next to a round glass-top table with a beer in his hand. He was wearing shorts and a tasteful hawaiian shirt, had wire-rimmed glasses, and a neatly trimmed white goatee even though the hair on his head was still brown. As Fiona turned off the engine and unbuckled her seatbelt, he put his beer down on the table, got up, and walked to the edge of the patio, waiting to greet us.
We both took off our sunglasses and put them in the center cubby. Fiona looked in the rearview mirror and fluffed her hair. I started to put my sandals back on but she said “Don’t bother.”
She opened her door and stepped out first. I followed her lead and stepped out on the other side so the car was blocking me from view at the moment. She took a few steps along the stone path to the patio and the man opened his arms to greet her.
“Fi, so glad to see you, it’s been too long,” he said and grabbed her in a big bear hug.
The concrete driveway was warm and grainy under my bare feet. I was nervous about taking the next few steps around the front of the car which would put me in his line of sight. I hesitated briefly as I watched his hands roam over my girlfriend’s back and down to her thinly covered ass, making her giggle. Finally, I took a deep breath and stepped out onto the path, exposing myself. I had been naked in front of her friends and my friends and even my sister before but right now I felt so vulnerable.
The stones felt smooth and worn compared to the driveway. I paused a couple of paces behind Fiona and waited awkwardly as I glanced around taking in the surroundings.
There was a relatively high wooden fence around the perimeter of the yard, but I could see several houses with second-story windows that would have a pretty good view if anyone happened to be looking out. There was a small in-ground pool on the other side of the patio, several trees and shrubs, and a nice vegetable garden behind the garage, but nothing that would provide any significant cover. Despite the warmth of the sun on my bare skin, I shivered. Fiona had been generous in calling it secluded, I thought.
Carson finally released Fiona from the embrace but he kept his left arm around her waist, possessively, as they both turned to face me. My heart was pounding in my chest. I normally wasn’t anxious about meeting new people but this man suddenly seemed larger than life.
“Carson, this is my boyfriend, Brian,” she said.
He tilted his head down to look at me over the top of his glasses.
“Brian,” he said in a deep voice and put out his hand, “it’s good to meet you.”
I realized I was fidgeting and made myself stop as I stepped forward and shook his hand. It was a firm manly handshake that further defined the dichotomy of our status. Not just that he was clothed while I was completely naked, but his calm attitude and presence. I also noticed that pumping his hand made my caged cock jiggle. I tried to speak but my mouth felt dry and no words came out.
After releasing my hand he turned his head toward Fiona.
“May I?” he asked, gesturing in my direction.
“Of course,” she said, but Brian detected a hint of hesitation in her voice. Was she afraid that I might not meet her mentor’s expectations?
He removed his arm from my girlfriend’s waist and focused on me.
“Inspect,” he commanded.
It was obvious that he expected me to react to this instruction but I had no clue what to do. It made me even more anxious that I did not know the protocols.
“He’s not my slave, Carson. I haven’t trained him to respond to those commands yet,” Fiona explained.
Yet? I thought, my eyes darted towards Fiona but otherwise I didn’t react.
“Really, Fi? Those were some of the first things I taught you,” he said, a little surprised.
“Yes, well, you were always a little old school,” she jibed.
“Ha, well, stick with what works, I say,” he grumbled, then addressed me.
“There are some key commands that you should be aware of if you are going to be mixing in the community,” he instructed. “For example, when I say ‘inspect’, you should stand up straight, put your hands on your head, and spread your feet a little more than shoulder-width apart. Got it?”
“Y-yes…sir,” I said, barely finding my voice. I wasn’t sure but it felt appropriate to call him Sir.
“Well, go on, then. Inspect,” he said again with a hand wave in my direction.
I quickly positioned myself as he had instructed. He kicked at the inside of my left foot and I slid it a little farther out. I could smell his cologne as he looked me up and down. I felt even more exposed now putting myself on display like this out here in the open feeling like I was already failing some exam that I hadn’t studied for.
“Smooth all over, I see, just like I taught you,” he said, obviously addressing Fiona and not me. I nervously glanced at Fiona trying not to move in case that was some sort of transgression.
The observation made me feel even more naked if that was even possible. Did I see a curtain move in one of the neighbor’s windows? I was having a hard time standing still. Some part of my brain was screaming that I should turn and run for the car and hide.
He grasped my caged cock, causing me to emit a small “ooh”, but I didn’t move. He looked it over and weighed it in his hand for a minute.
“That’s a nice cage, it seems like the perfect size for him,” he said.
“Yes, it was 3D printed to his exact measurements,” she replied.
“Oh, so high-tech,” he said in a mocking tone.
I could feel my cock trying to grow from his manipulations.
“He is doing a good job filling it out too,” he observed with a chuckle. “How big is his cock when he is fully erect?”
“Five and a half inches,” Fiona said.
“Not bad, that’s about average,” he said. “Why did you lock him up? Are you going to try and shrink it?”
“No. Tell him why, Brian,” she ordered.
I swallowed hard. I had already explained several times whenever someone had asked, and it never got any less embarrassing. This was harder, not only because I barely knew this man, but because I also wanted his approval. I felt like I was meeting Fiona’s father. Maybe he was in some ways. He had mentioned her training a couple of times already, maybe there was more to their past than I had realized.
“I had…” I started to say but my mouth was so dry again that it came out as a rasp. I swallowed hard and tried again.
“I had an orgasm without permission, sir,” I began, avoiding eye contact with either of them, “and then I tried to clean it up and not tell Fiona.”
“Oh, I see,” he said, “well, this punishment seems fitting then. Good choice, Fi.”
He released my member and then held up his hand.
“He seems to be enjoying this,” he said, showing his hand to Fiona and chuckling. “Reminds me of how wet you used to be during your inspections.”
Her inspections echoed in my head and I let out a small gasp. Had she been his submissive? I looked at Fiona. Was she blushing a little?
My attention was brought back to Carson as he raised his hand to my face. Without being told, I stuck out my tongue and licked the drops of my precum off of his palm even as I blushed so deeply I thought I could feel the heat radiating from my face.
“Good boy! You taught him to eat his own cum, I see,” he said, glancing at Fiona, then at me, adding, “You are making her proud.”
I looked at Fiona and she was smiling, but Carson wasn’t finished with me yet. He went back to his instructor’s voice.
“Now, when I give the command ‘present’, I want you to turn around and face away from me and bend over at the waist. Keep your legs apart and reach back and spread your ass cheeks,” he explained, “Can you do that?”
“Umm…yes, sir?” I said, hesitantly, as I glanced at Fiona.
“You don’t have to get her permission, I already asked her before we started,” he said in a direct tone.
Fiona seemed nervous, biting her lip a little but gave me a nod.
“Yes, sir,” I said, trying to sound more confident.
“Present,” he commanded.
I fumbled a little trying to turn around, then discovered it was harder than I expected to bend over at the waist with my legs spread. I had to bring them a little closer together but I finally managed, then I struggled to reach back and get enough of a hold to pull my cheeks apart because my hands were sweating. When I finally felt it was as good as it was going to get I stopped moving as much as possible and waited.
Even though practically everyone we knew had seen my plugged ass before, this had to be the most humiliating thing I had ever done and I understood why the command was ‘present’. The green jeweled plug would be the centerpiece of my compromising presentation, but I could also feel the sun warming my balls as my enclosed manhood swung freely between my legs.
“Good boy,” he said, patting me on the ass, “That one can take some practice. You are doing well for your first attempt.”
I was surprised by the compliment. I hoped that Fiona was pleased.
He felt both ass cheeks and then rubbed around the plug before tugging on it slightly.
“How big is it,” he asked.
“One and three-quarters,” she said. “He should be ready for a full two inches soon. That’s my goal.”
This was the first I had heard of that goal.
“That’s a good size. Two should keep him opened up so he can take pretty much any cock,” he said.
I felt my fingers starting to slip and had to grab a little more ass to hold on but no one seemed to notice.
“Do you fuck him regularly?” Carson asked.
“Yes,” Fiona said, “I’ve used my strap-on since shortly after we started dating and I let three of his friends open him up after his recent transgression. That will be an ongoing thing now.”
“Oh, so is he naturally bi?” he asked, sounding interested.
“He was reluctant at first, but I have turned him into quite the little cock sucker this past year,” she said smiling. “Those same three friends have helped me train him, and the best part is he is always blindfolded and tied up so he doesn’t even know which of his friends he has been swallowing.”
They both laughed and Carson said, “Well done.”
Suddenly I felt his hand cup my balls. He rolled them around and pulled and squeezed them a little. I winced but did not move. He wasn’t hurting me, but we men are somewhat protective of our balls.
My shame at being fondled by this man right here in his yard in front of my girlfriend (and anyone who might be looking out their windows) was almost unbearable. I was feeling a bit light-headed, whether from the emotions or the position, I wasn’t sure. He continued to feel me up for what seemed like ages while I tried not to squirm before finally releasing my scrotum.
“Okay, stand up,” he said, “and let’s go into my workshop and see about making you a strap for that cage.”
I released my buttocks, shakily straightened back up, and stretched. I wasn’t in that position very long but it wasn’t comfortable.
Carson led the way to the side door of the garage and let us in. Sunlight streamed in from a couple of windows but he also flipped a switch by the door causing an array of bright fluorescent lights to flicker on. I felt some small relief that we were at least indoors now.
The garage was his workshop. There were a couple of tables and stools in the center of the room littered with scraps of paper and leather and partially finished projects. Workbenches ran along two of the walls meeting at one corner with a variety of tools hanging over them on pegboard hooks. There were also several shelves with more tools plus cans and jars filled with screws, metal parts, stains, glues, and so forth. A third wall was covered with long strips of leather in various widths and colors, plus a few larger sheets of leather, some with the brown fur still on the hide. An old motorcycle, partially covered by a plastic tarp, leaned on its kickstand near the roll-up garage door.
Carson picked up a short step stool and placed it near one of the tables.
“Stand on that so I can get some measurements,” he directed.
He pulled a worn dressmaker’s measuring tape out of a drawer as I stepped up to the top of the stool. This put my chastity right at eye level.
“Face that way,” he said, indicating towards the table. I turned so my bare ass was facing out into the room. He stood at my side and tucked one end of the tape measure under the base ring and folded it over.
“Hold that right there for me,” he said.
I pressed my finger firmly over the end so it wouldn’t slip as he moved around to the other side with the other end of the tape. He slipped this under the base ring on the other side and adjusted it so it was lying flat and taut around my waist just above the cleft of my ass.
“Write down 32 for me,” he said to Fiona and he undid both ends of the tape.
She looked around and found a pencil and a slip of paper on the table and wrote down the number. Meanwhile, Carson grabbed hold of my cage and used it like a handle to turn me around 90 degrees so my crotch was facing him and my ass was facing her
I am pretty much just a mannequin at this point, I thought.
He then proceeded to pull and wiggle the cage while examining it very closely, even bending down to look up from underneath. The motion was sending electric tendrils through my body, making me whimper.
“You said this strap was to keep the cage from moving around and causing him to chafe, right?” he said. “See how this ring moves down here?”
Fiona leaned down behind me for a closer look at my balls where he was indicating.
“Yes, I see what you mean. And that is one of the places he often got a sore spot,” she said, reaching up to touch where my scrotum met my perineum.
Fiona hadn’t allowed me to cum for quite a while and all of this touching and groping and jiggling was starting to affect me. I could feel the beginnings of an orgasm rising and I moaned a little louder than I intended, but it got my message across. Carson stopped and let go of my organ, leaving me on the edge.
“I guess it’s been a while?” he asked, chuckling.
“Yes, what’s it been…almost two weeks?” she asked, dragging her fingernail across my ass.
“Uh huh,” and nodding was all I could manage as I was still trying to tamp down my body’s desperate need to climax. There was no way I was going to embarrass myself or Fiona by shooting my wad in front of him without permission.
“Let’s give him a minute to calm down and talk about some options. I recommend a strap up the back as well,” he said. “You see this a lot on harnesses for horses or dogs where there isn’t enough support in one area so the whole thing shifts around when they are walking or running, and anything that moves like that will eventually rub a raw place on the skin.”
“So it will be like a thong?” Fiona asked.
“It can be. We’ll have to use some softer material for that and maybe make it round through here,” he explained, rubbing his finger lightly between my cheeks, “so it doesn’t rub in there.”
“Okay,” Fiona replied.
“But I can also make a few other things so you can have some different options. For example, I can do a strap with a wide panel here,” he used his thumb and forefinger to spread my ass above the plug. “That would hold a larger plug or dildo in place so it can’t slip out. It would be perfect for training with dilators.”
“Oh, I like that idea!” she said excitedly.
“I guess you’ve forgotten how much you hated the dilators, but I highly recommend them,” he said.
I wasn’t entirely sure what dilators were but it seemed there had been more between her and Carson than she had told me so far. My thoughts were disrupted as Carson started touching my perineum about halfway between my balls and my asshole.
“I can also make one that Ys off here,” he said, “then two straps up across each cheek, leaving his hole open for use or at least his plug unobstructed.”
“Nice! Kinda like a jockstrap,” she said.
“Yes, exactly,” he said.
Despite the teasing, my pending orgasm had mostly subsided as Carson proceeded to use the tape to make additional measurements which required him to handle my balls and ass in various ways. I was able to keep myself in check this time, with only a few more low moans, by trying to focus on some of the objects in the room as a distraction.
That motorcycle looks cool, I wonder if it still runs, I thought to myself, and Oh, look, he has a skylight. I wonder if the landlord would let us install one of those in our apartment.
“Now you just need to pick colors and any design you might want,” he finally told her, my torture apparently over for now.
Carson and Fiona wandered over to the wall with all the leather strips and he showed her several different options. Meanwhile, I was left standing there on the stool like a model for an art class. No one had told me I could get down from the stool. Should I join them? Am I allowed to express my opinion? I decided to stay where I was and just listen quietly.
In the end, she chose to go with a reddish-brown color for the leather with a celtic knot imprint and silver hardware.
“It will take me about a week to put it all together,” he said after he had written down all of her choices.
“Aww, I was hoping to get at least the basic strap today,” she said, pouting more than I had ever seen her do. She was definitely a different person with Carson.
“Rome wasn’t built in a day, darling,” he said, “but that just means you have to come to see me again!”
“I guess,” she replied, pushing out her lower lip but then turning it into a smile.
“How about we go have some lunch,” Carson said, “Brandy should have everything ready by now.”
With everything else going on, I had forgotten about his wife, Brandy. Fiona had never said much about her, just referenced them together. Yet another person who was going to see me naked today.
The two of them started towards the door, I was still standing on the stool and made the command decision to step down and follow.