Chapter 8

I stepped out of the shower onto the soft fuzzy mat, pulled my towel off the bar, and began drying myself off. I always start with my short brown hair and then work my way down my shoulders, arms, and chest. I looked at the full-length mirror that was attached to the back of the door, but it was covered with steam so I gave it a wipe with my towel...

I’m not a model or some musclebound jock. I try to keep in shape with a few exercises at home and playing basketball and racquetball with some of my buddies. My body is slender and sometimes I think I still look like a kid. The complete lack of any body hair doesn’t help. My girlfriend, Fiona, likes it that way and I use a special cream in the shower to keep most of the hair from growing at all, and what does is very sparse and fine so it’s easily removed. My skin almost glows, I am so pale.

I threw one end of the towel over my shoulders and let it cascade down my back. I had dried my back this way since I was a kid and it always made me think about running through the house in my Batman underwear with a towel as a cape. I wondered what superhero I would be since Fiona required me to stay naked all the time now.

My pale bare skin also made the black plastic cage that encased my cock really stand out. It had been several weeks since Fiona had removed the cage and allowed me to fuck her sweet ass. Since then the cage hadn’t been off and I hadn’t been allowed to cum. I had eaten Fiona’s pussy dozens of times and had also been fucked twice by my buddies (I still had to be blindfolded so I wouldn’t know who they are) and of course, they always finished in my mouth. It felt so slutty to take a cock straight from my ass into my mouth, but I loved hearing Fiona tell me I was a good boy for swallowing all of their cum.

When I finished drying myself, I rubbed a small dab of leave-in condition into my hair and brushed it back. It was already almost dry. I applied lotion to my whole body, especially around the base ring of my cage to help prevent chafing. Then I put on the custom leather waist straps that Carson, Fiona’s friend and former mentor, had made for me. I had removed the straps for the shower to keep them from getting too wet.

Before she left for work, Fiona had told me to add the dildo strap today and laid out a realistic-looking dildo that was about seven inches long and slightly thicker than my own cock (when it wasn’t locked in chastity). She had been making me use this one a lot lately. Unlike a butt plug, it did not have a narrow shaft that allowed my sphincter to almost completely close after the larger head was in my rectum to help with retention. Instead, it had a straight shaft that was the same size all the way down so my sphincter muscles would remain stretched around it the whole time it was in. This extra strap ran from the bottom of my chastity ring, up between my ass cheeks, and then attach to the waist strap and had a special pad that held the base of the dildo in a little pocket. Once everything was attached, it would keep the dildo pressed firmly into my anus.

It required a bit of maneuvering to get it done. First I used a small syringe to shoot a good amount of lube up into my anal passage. I attached the dildo to the pad and then coated it in lube as well. I attached one end of the strap to my chastity ring behind my balls while the heavy silicone cock swung between my legs. Then I reached around and slid the pad along the strap until I had the head of the dildo lined up with my rear orifice. I relaxed as much as I could and then worked the fat head of the dildo into my hole. As it slid deeper, I exhaled, but it came out as a low moan. I worked it in and out a little to try and get it to settle into place before finally forcing the full seven inches inside until the pad was pushing my cheeks apart. Then holding it in place as best as I could, I brought the other end of the strap up to my waist and worked it around the strap there, snapping it in place. Carson had taken careful measurements before making the straps so it was exactly the right length to keep the dildo from moving more than an inch or so – just enough to tease my hole whenever I moved around, but especially when I was sitting on it.

I squirmed, trying to get accustomed to the thick shaft that would keep both of my sphincter rings stretched. When we first started using the dildo I couldn’t go very long before the ache became too much for me to stand but, like any other muscle, as it was used more and more, I was able to keep the dildo in longer and longer. I would still be aching by the end of the day but I would be able to keep it in until Fiona decided it could be removed.

To that end, I had one last task to perform. The snaps had been designed with a small hole where a small post could be pushed through so a lock could be attached. Fiona knew that she could trust me but she liked the idea that, once locked, there was no way for me to remove the straps or the dildo without the key that she kept with her. So, as she had instructed, I went around to each of the four snaps – one on each side of my cage, one where the strap in the back attached to the waist strap, and the last one where the dildo strap attached behind my balls – and locked it in place with a tiny lock. The little snick of each of the four locks was just a further reminder that I belonged to Fiona. The one at the base ring would be the most annoying because it would be wiggling between my legs all day.

Finally “dressed” for the day, I walked a little bow-legged to the kitchen to finish my morning chores before I had to sign on to work. The movement helped the dildo settle in so at least I could walk normally. Sitting was still uncomfortable, but Fiona had recently got me one of those stand-up desks for work and she said I didn’t need to be sitting around all day anyway since her job at the gallery kept her on her feet most of the day.

The rest of the day was pretty uneventful. My ass was throbbing so I was glad when I heard Fiona’s voice in the hallway outside our loft. I couldn’t hear what she was saying but she was probably just exchanging pleasantries with our elderly neighbors. They would often poke their head out when they heard the rickety old elevator reach our floor.

I got up from my desk and walked over to the door to greet her as I heard her put the key in the lock.

“Hey, babe, I...” I started to say as the door opened, but then I realized she wasn’t alone. Fiona held the door as her old mentors, Brandy and Carson, followed her in.

“Brian!” Carson said, smiling, and stuck out his hand. “I’d ask how it’s hanging but I can see for myself.”

We both chuckled as we shook hands. I liked Carson, he was just a nice guy. You always knew where you stood with him, he didn’t play games and pretty much just said what he was thinking.

Brandy, on the other hand, just looked me over like she wanted to make me stand at attention for an inspection and that probably wasn’t far from the truth.

“Let me take your coats,” I offered.

Carson slipped his light jacket off and handed it to me. Brandy waited for me to help her take hers off. Fiona also handed me hers and I hung all three of them up on a row of hooks near the door while the three of them settled into the living room area. Brandy and Carson took the sofa and Fiona took the chair at the end next to Brandy.

“Brian, can you fix us some drinks?” Fiona asked. “I’ll have some of that new wine we got the other day.”

“That sounds fine,” Brandy said.

“Carson? Whiskey?” I asked. I knew what he liked.

“Of course!” he replied.

I walked over to the kitchen and pulled out the bottles and glasses to make the drinks while they continued the conversation they must have started before they came in. The surprise of Brandy and Carson’s arrival had made me forget about my aching ass for a few minutes but bending and reaching caused the dildo to push in and out of my ass and I had to stifle a moan.

I carried the two glasses of wine over along with the bottle first, handed Brandy and Fiona a glass, and then put the bottle on the table between them. I turned to go back to the kitchen to get the whiskey for me and Carson’s, giving everyone their first good view of my ass.

“Hey, you are using the dildo strap I made!” Carson exclaimed. “How is that working out?”

Picking up the two glasses of whiskey, I started to reply but Fiona answered instead.

“It’s great! We have been using it a lot and I love how it keeps his hole stretched so much better than the plugs.” Fiona said and motioned for me to turn around so they could see it better.

I handed Carson his glass and sat mine on the coffee table. Then, standing between Fiona and Brandy, I turned, bent over at the waist, and reached back to pull my ass cheeks apart the way Fiona had taught me. Holding myself open gave me some momentary relief from the pain, but my sphincter was so sensitive I could feel the dildo shifting slightly with every breath I took.

“Good boy,” Fiona said, making me smile.

Brandy reached out and tugged on the strap, pulling the dildo out a little. I inhaled sharply and then tried not to groan, but failed, as she prodded around the swollen sensitive ring where it was stretched by the dildo.

“He seems to be taking it well,” Brandy said. “How long has it been in today?”

“He was taking his shower when I left so what time did you get it in, sweety?” Fiona asked.

“It was about 8:30,” I grunted as Brandy pushed the dildo in as far as it would go, forcing me to brace my shoulder against the table beside me to keep from falling over.

“That’s pretty impressive,” Carson said, “I’ll bet your ass is really aching by now.”

“Yes, Sir,” I said followed by another sharp intake of breath as Brandy pulled the dildo out as far as the strap would allow.

“I love that the straps are locked in place,” Brandy said as she reached between my legs to tug on the lock behind my balls.

“I don’t really have to, he’s never tried to take it out without permission,” Fiona said, reaching around to my front to flick one of the locks beside my cage, “but I think it sets a tone, especially when his friends come around and see the little locks.”

I closed my eyes and tried to calm myself. I wanted to cum so badly I could almost have cried. My poor caged dick was futilely trying to grow inside the cage. I whimpered a little as Fiona’s finger brushed against the sensitive bare flesh that was squeezing out of the gaps and when Brandy’s fingernails scratched lightly at my swollen scrotum, I had to bite my lip...

“You girls are going to have him making a mess on the floor if you keep that up,” Carson warned.

I opened my eyes and looked between my legs and I could see a long string of cum already leaking from the tip of my cage.

“You better catch that,” Fiona said.

I released one ass cheek and collected the gooey strand with my fingers, then, as I had been taught, I stuck them in my mouth and sucked them clean. As I savored the salty-sweet flavor of my semen, I reached back and spread my ass apart again. I had learned to crave the taste of cum, especially my own, but it was still mortifying to have other people see me do that.

Brandy and Fiona both withdrew their hands leaving me panting and desperately wanting more.

“I think you should make those for both of our new submissives,” Brandy told her husband.

“I can do that, no problem,” Carson replied.

“You can go and sit down now,” Fiona said giving me a little slap on my ass.

I straightened up, grabbed my drink, and went to the loveseat directly across from Brandy. I gingerly lowered myself onto the seat and sighed as it pressed the dildo’s last inch or so into me. I sat upright without leaning against the back cushion and crossed my ankles with my knees spread so my cage would be on display, just the way Fiona had taught me.

Fiona gave me a small nod of approval that didn’t go unnoticed by Brandy.

“I have to admit you have done a good job with his training,” Brandy told Fiona.

“Thank you, that means a lot coming from you,” Fiona beamed, “but he deserves a lot of the credit. He always tries to please me and has never put up much of a fight. He is almost a natural born submissive.”

I blushed and looked at Fiona warmly. I loved her so much, of course, I would do anything to please her. Some things had been more difficult to accept than others – the full-time nudity, the hairless body, and now the anal training, but it was the bi training that had been the most humiliating. Before I met Fiona I had no desire to suck another guy’s cock, much less take one in the ass. Now I was doing it regularly and even asking for it.

As if he had read my mind, Carson chuckled and said: “He has certainly become quite the cock sucker.”

Everyone laughed, including me, but my face reddened further and my mind was racing. The first time I met Brandy and Carson I sucked Carson’s cock while the girls watched. And then I did it of my own accord when he dropped off the leather straps I was wearing. Was I going to be sucking Carson’s cock again this evening? I thought of having to crawl over between his legs and take his cock out while Fiona and Brandy watched. I wouldn’t mind, he had a very nice cock...

I tried to steal a glance at Brandy but she seemed to be watching me but, for once, it wasn’t her usual steely glare. She was a very attractive woman even if she was probably 10 or maybe even 20 years older than me. She was wearing a loose-fitting top and yoga pants which showed off her toned ass and legs, but I wondered what she would look like naked. Would she be shaved? Probably a landing strip at most. Would she taste as good as Fiona? My cock was beginning to strain against its cage as I thought about my tongue lapping at the warm folds of her vagina.

“I thought we could order dinner from this good asian-fusion place nearby,” Fiona said, breaking me out of my daydream.

“That sounds lovely,” Brandy said, “Just order family style, you remember what we like.”

“They are really popular right now so it takes a while for them to deliver,” Fiona said taking out her phone.

“That’s okay, it will give us time to check out your room,” Carson said, smiling and looking at Brian.

“Yes, please,” Brandy said. “He hasn’t stopped talking about it since Brian showed it to him the other day.”

“Of course!” Fiona said brightly. “Brian, you can show them while I order the food.”

“And be a good boy and do as you are told,” Fiona whispered while looking into my eyes over the top of her phone.

I led Brandy and Carson down the short hall past the bedroom to the last door.

“We just call it The Room,” I explained as I opened the door and pushed it open.

After flipping on the light switch, I allowed the two of them to enter first then stepped in after. They both glanced around at all the toys and stuff on the shelves and hung on the walls, but their attention was mostly on the antique medical chair that was mounted in the center of the room.

“See what I mean? It’s a great piece,” Carson said as Brandy examined the chair. “Brian did the custom welding work on it.”

Carson put his arm behind my back and nudged me forward. His hand was warm against my bare skin.

“This is very nice!” Brandy said as examined it closely. “Fiona said it was just a lucky find at an antique store?”

“Yes, we were looking for some furniture when we first moved in here and just stumbled onto it,” I said. “As soon as she saw it she had to have it.”

“It is in great shape,” Brandy remarked, stroking the leather seat and back.

“Well, we had to put some work into it. You can see where I welded the base there,” I explained pointing out the repair, “and I added all these tie-down points. Brandy had a friend redo the cushions.”

“Is it fully functional? The stirrups and tilt and everything?” Carson asked.

“Yes, it took some oil and sanding to smooth everything out but now all those joints are like butter,” I said, smiling proudly at my handiwork.

“Maybe we could have a little demonstration,” Brandy suggested.

“Sure!” I said and worked my way around the chair showing them the various knobs and levers that would allow the chair and stirrups to be moved into different positions, ending with the back lowered so it was completely flat.

“And the headrest can be dropped like this, to allow, umm...” I hesitated and blushed, thinking about how many times my head had been hanging off the end of the chair to allow my friends a straight shot to shove their cocks down my throat, and at that moment I couldn’t think of any other purpose.

From the smiles on their faces, I was sure they had a pretty good idea what that feature was used for, but Carson jumped in before I could find the words.

“I think we get it,” Carson chuckled, “but I think we might need to really see it in action.”

“Yes, why don’t you set it back up and then get in the chair and let us give it a try,” Brandy said, patting the seat.

I glanced towards the doorway hoping Fiona might come to my rescue, but it was empty. Only her last command had followed me into the room – be a good boy and do as you are told.

“Uhh, sure,” I said, my heart starting to pound a little. Had this been the plan all along or was this just some spur-of-the-moment thing? Fiona’s instructions had been very clear, so I decided to go along with it.

I configured it back into a chair with the back upright and then sat on the seat and, pushing against the armrests, slid back until I was fully against the back. My legs went automatically into the stirrups which were down at the moment.

“I believe Fiona makes you wear a blindfold when your friends are here, is that right?” Brandy asked, taking a black leather blindfold from one of the pegs on the wall.

“Y, yes ma’am,” I said nervously.

“You can strip,” Brandy said to Carson as she retrieved a black leather blindfold from a hook on the wall.

The last thing I saw was Carson starting to unbutton his shirt before Brandy placed the blindfold over my eyes and fastened it tightly around my head. It was followed by a fat penis gag that was also fastened around my head with a leather strap.

I could still hear the rustle of clothes being removed and from the whispers and mumbled words I could hear, Brandy was getting naked as well. My earlier thoughts about what she might look like naked returned even more vividly than before and my cock strained against its limits even more.

Once they had reached their desired state of undress, cords were wrapped over my forearms and wrists as they tied them tightly to the armrests. They were working together, one on each side. The straps for the stirrups were fastened around my legs. The stirrups were more of a tray that the calf rested in and did not actually restrain the feet. Next was a rope across my body going from a tie-down point above my right shoulder, across my chest to the left side by my waist where they pulled it tight and tied it off. Then they followed the same procedure across my waist to the right side, then back up and across my chest to the left shoulder, and finally across my neck to the starting point. They worked together with practiced efficiency and I imagined that I could feel the heat radiating off of Brandy’s naked body whenever she leaned over me. When they were done I had almost no freedom to move.

The final touch was a set of clamps attached to my nipples. I groaned as each one was attached, then again as the chain was pulled down in the middle with another chain connected to my chastity cage to keep a little tension on it.

“Alright, let’s see what this baby can do,” Carson said.

They tilted the chair a few different ways, just playing around with the different options and making comments about how it exposed me and what things they could do to me in those positions. In addition to the humiliation, all that movement made the clamps tug on my nipples, causing me to moan into the gag. I could also feel droplets of cum leaking from my engorged cock, as it continued to futilely demand freedom.

They finally finished with me completely vertical and the stirrups adjusted so that my legs were up as high as they would go and spread as far apart as they would go. I knew my chastity and plugged ass were on full display.

“Comfy, Brian?” Carson asked, chucking, his voice coming from behind my head.

“Mmmm ugggh owfff,” was all I could manage to say with the gag still filling my mouth.

“Help me with this,” Brandy said, and I could hear them moving around but had no clue what Carson was helping her with.

“Do you think this is too much?” Brandy asked.

“I don’t think so,” Carson said, “He’s a good boy, I think he can take it.”

My brain was going crazy imagining all the things in this room that might be considered ‘too much’ and what they could do to me in this humiliating and helpless condition. I couldn’t even call out to Fiona, but even as I thought about that I knew that she would be very disappointed if I did.

WHACK!

I screamed into the gag as much from surprise as the pain when a heavy wooden paddle connected with one of my ass cheeks. I tried to shift my ass to one side or the other but I could hardly move.

“I love how this keeps him in the perfect position!” Brandy said. “It’s even better than our spanking bench.”

WHACK!

Brandy landed a second blow directly on top of the first, and I screamed again. She continued to redden every inch of my buttocks. Some of the strikes landed on or near the dildo that was still strapped deeply into my rectum, causing the aching ring of muscles to clench against the invading shaft and my whole body to clench.

While Brandy worked mercilessly on my ass, Carson unfastened the gag and pulled it out of my mouth. I swallowed and breathed heavily through my mouth as he lowered the headrest allowing my head to tilt back and giving him a straight shot through my mouth and down my throat. I cleared my throat, preparing for what I knew was coming.

“She really likes your chair,” Carson said. “Fiona said it would be okay if we had a little fun with you this evening. I hope you don’t mind.”

I wanted to say “No, Sir, I don’t mind,” but “Nnggg,” and me nodding my approval was all I could muster.

“I’ll take that as approval,” Carson said, chuckling, “not that you have much choice at this point.”

I started to answer but when my lips parted his cock was right there. It was already hard and he had no trouble pushing it all the way to the root in one slow motion. He held it there with his smooth balls covering my nose and let me get accustomed to it in my throat before he started to move. He only rocked back about an inch or so before pushing it back in again. This kept the head of his cock in my throat the whole time. I had gotten pretty good at deepthroating my friends and I had learned to suppress my gag reflex almost completely, but this technique was challenging and my throat was contracting with each forward stroke, milking his member.

“Mmmm, that’s a good little cock slut,” Carson moaned, enjoying the sensation.

Distracted by Carson’s cock, I hadn’t realized that Brandy had stopped beating my ass with the paddle. I sighed, thinking the worst was over.

THWICK!

She had switched to a thin cane and began to slowly work her way up the back of each of my thighs. The pain combined with Carson’s fat cock tickling my throat was bringing tears to my eyes behind the blindfold. There was so much going on at both ends of my body that I couldn’t keep track of it all. She finally stopped just before I reached the point of actually crying or passing out, I wasn’t sure which. Carson did not stop and was almost humming as he enjoyed the spasms in my throat.

THWICK!

Apparently, she wasn’t done yet! I had never had anyone use a cane (or anything else) on the bottom of my feet before. It stung in a way that was exquisitely different from the way it felt on my ass and thighs. I wiggled and twisted my foot as much as I could trying to ease the pain.

“That won’t do,” Brandy said.

A moment later she took my foot in her hand and looped a cord between my toes. She pulled it towards my leg as far as my foot would bend and then she tied it off below my knee. She did the same with my other foot. Now I could barely move my feet at all.

THWICK!

Another stroke of the cane across the bottom of my foot. I yelped with Carson’s cock blocking most of the sound. Having my foot stretched seemed to make it even more intense.

“Just hang in there, my boy,” Carson said soothingly and caressed my cheek slowly down to my neck where, to my amazement, I could feel him stroke his cock through the bulge in my throat as he continued to use me as his personal cock sleeve.

Alternating every few strokes, Brandy laid a dozen or more stripes across the bottom of each foot before she was done.

I could feel the head of Carson’s cock growing slightly as he watched her torture my feet and I knew this was a sign he was close to reaching orgasm but I guess he wasn’t ready to cum so soon (or maybe he needed permission from Brandy) so he pulled out, giving me a chance catch my breath, and swallow some of the spittle that had been spilling out of the sides of my mouth while he used me.

I could still feel the stinging welts on my feet and the back of my legs. I was imagining what they looked like. I was certainly going to be sore for a few days after this. Fiona had left marks on me on many occasions in the past and I remembered how my friends thought it was funny when they would see them and tease me, asking what I had done to earn such a punishment and Fiona would always expect me to tell them. It was utterly humiliating but I had taken it all in good fun and hated that I found it arousing to reveal such intimate details. Fiona didn’t seem to mind them knowing about the things we did, it was almost a point of pride for her and, of course, they never teased her about it.

I was abruptly brought back from my musings when Brandy wrapped her hand around my balls. They were quite sensitive and a little swollen after not being allowed to cum for several weeks. I moaned as she kneaded them gently with her hand. After a few moments, she moved farther down and pulled at the lock for the strap behind my scrotum. After a little jiggling, I heard a small click as the lock was opened. Fiona must have given her the keys. She removed the lock and unsnapped the strap from the base ring.

The manipulation of the lock and strap sent small tingles into my sore stretched anus, making me squirm as much as my bondage allowed. When Brandy pressed on the bottom of the dildo, forcing it as deep as it would go, I cried out and then began to whimper as she slowly withdrew it. It made a wet sucking sound, as my tortured ass betrayed itself and clung greedily to the shaft. Just as I felt the head about to pass through my sphincter, she slowly drove it back to the base again, and I groaned loudly the whole time, feeling every inch.

“God, I love watching his ass grip that thing,” Carson said, apparently having moved around next to Brandy to watch as she repeated the process several more times.

“I think he looks about ready, don’t you?” Brandy asked. I was too lost in the mixture of pleasure and pain to even wonder what I might be ready for.

On the next withdrawal, she pulled it all the way out with a literal pop as the head was freed from my hole. I sighed feeling my sphincter muscles able to relax for the first time since I got out of the shower this morning. I could only imagine what they were seeing since my anus would be gaping open for a while.

“Let him clean this off,” Fiona said.

I could feel the lube and god knows what else leaking out of my ass. Despite my thorough anal cleanings, the dildo was always covered with slimy lube and the occasional fleck of other stuff after it had been locked in my ass for an extended period. As Carson approached my mouth with the dildo, I could smell it before it touched my lips. I had done ass-to-mouth many times when my buddies had fucked my ass but Fiona had never made me lick the messy dildo clean after it had been in my ass all day. At this point, I was effectively drunk on hormones and adrenalin so, without being told, I opened my mouth and began licking and sucking on the dildo. Carson moved it around and made sure I was able to lick and suck the whole thing. It wasn’t as bad as I expected. Maybe one of them had wiped off the worst of it. Regardless, I tried to get it over with as quickly as possible.

“Good boy,” Carson said, finally taking it away from my mouth. “Fiona would be so proud of you.”

I smiled knowing that she would be pleased.

While I was cleaning the dildo, there was the sound of a bottle being squeezed and a moment later cool soothing gel was applied to my asshole, but if I thought that it was just out of kindness, I was sadly mistaken.

As Carson took the dildo away, I felt a new object pressing against my anus. I couldn’t tell what it was at first, it was large and felt cool but it wasn’t metal. I thought maybe it was something to soothe the raw orifice, but as Brandy pushed harder, it started stretching me again, then more and more. I was being stretched to my limit. I whimpered loudly as she slowly penetrated me with another dildo, but this felt like it was twice the size of the one I had been wearing earlier.