Fiona and Brian Chapter 8 — Shared in the Chair

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 diameter its whole length 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.

“They probably aren’t necessary, 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.

“Oh god! Oh! Oh! So big!” I cried out and I tried to thrash and get away but I was held firmly in the chair as the fat rubber cock was slowly but firmly forced into me. After being stretched all day, my sore sphincter raged at this new violation. I had never felt anything so intense before in my life, and it seemed to go on forever before I finally felt Brandy’s stomach press against my chastity.

“Wow, I can’t believe he took the whole thing on the first try!” Carson exclaimed.

“Mmm, yes, you know how much I love to stretch a tight little ass.” Brandy practically purred.

“I do know – from personal experience,” Carson chuckled.

“You’d better get back up there and put that mouth to some better use than just screaming because I’m going to fuck the shit out of him as soon as I get this settled in,” Brandy told him.

“I will, I just want to watch him take it one more time,” Carson said.

Brandy slowly pulled completely out and there was a loud sucking sound as the head pulled out of my ass. I could feel cool air entering my empty stretched rectum as I heard the lube bottle again.

“Are you ready, do you have a good angle?” Brandy asked.

“Yes, go for it,” Carson said, and I heard a beep. Were they recording this?

For a moment, I was mortified by the thought of them making a video of me being impaled by this elephantine cock, but all thoughts were driven from my mind as the strapon was driven slowly but steadily into my asshole again. I was breathing in short bursts like the way they teach women in the birthing classes. 

It seemed like it was 10 feet long and I was fully aware of every inch stretching my ass. Once I had taken the entire length again, she started to work it in and out slowly. Not the full length, just a few inches out and then back in.

“Oh, fuck,’ I moaned, “fuck me, fuck me, fuck me.”

“He is a real anal slut,” Brandy said, starting to move a little faster. “Liste to him beg.”

I wasn’t actually begging her to fuck me, it was just an exclamation, but I just moaned instead of correcting her.

Carson was back in front of my face again. He fed me his balls this time while he stroked his cock. I sucked and licked his scrotum sloppily, hoping to distract myself from the anal reaming I was receiving, but it was no use. Brandy continued to piston that beast into my ass and it was driving me insane.

I thought I would show off some of my skills and I snaked my tongue back across Carson’s perineum to his asshole. To my surprise, I found that he was wearing a metal plug in his ass.

“We’ll have to save that for another time,” Carson said in a low voice as he pulled back and placed the tip of his cock on my lips. “Are you ready to get fucked in both holes?”

“Yes, Sir,” I groaned as Brandy switched her pace to longer slower strokes that were even worse than the short faster ones.

Carson fed his cock to me and I sucked and licked the head and shaft using everything I had learned while sucking my buddies’ cocks. He didn’t bury it in my throat like before, he just moved his hips forward and back slowly and let me do the rest. I had him close to reaching orgasm sooner than I expected. He pulled out for a moment to hold off a bit longer.

Despite how sore my ass was and how big this strapon was, I was starting to feel more pleasure than pain as Brandy continued to fuck my ass. She continued to change the speed and length of her strokes so I couldn’t just settle into a rhythm and that was driving me crazy. I wanted to move to meet her thrusts with my own but I was tied to the chair. Her thrusts were making my cock and balls flop back and forth and the constant rubbing and pressure on my prostate had me leaking so I could feel the droplets of precum landing on my stomach. Every sensation was in a heightened state. That’s when I realized too late that I was rapidly approaching my own climax. Normally I wasn’t allowed to cum without permission but this one snuck up on me.

“Oh, fuck, I’m going to cum,” I grunted only seconds before streams of creamy semen started pumping out of my chastity cage, running down across my balls and onto the shaft of the strap-on. 

Brandy didn’t stop her thrusting but she grabbed my cage and massaged my balls to try and get as much out of me as she could.

“I’m fucking you with your own cum, slut” Brandy said, plowing my ass, and I could hear the sloppy wet sounds

“So fucking hot,” Carson growled as he penetrated my mouth again before I had a chance to say anything else.

I did my best to pleasure his cock but he was simply fucking my face this time. His balls were slapping against my nose and I probably would have gotten a black eye if I hadn’t been wearing the leather blindfold. 

It only took a minute before he was grunting and dumping what felt like buckets of cum into my mouth. I tried to swallow as fast as I could but it was not as easy to do with him still humping frantically. A lot of it ended up running down my cheeks and into my nose. Unable to breathe, I was choking on his cock when he finally stopped and pulled his dripping cock out of my mouth. It took several minutes of coughing and blowing cum out of my nose before I was able to breathe normally again.

Meanwhile, Brandy was still driving that massive dildo into my ass and it was starting to become more pain than pleasure again.

“Please, Ma’am, I can’t take anymore. Please,” I begged hoarsly. “I’ll do anything else, just please no more.”

Brandy slowed her pace and then withdrew the beast from my wrecked rectum. 

“I will take you up on that later,” she said to me, and then to Carson, “Help me get out of this harness.”

A few moments later, I heard Fiona’s voice from the doorway.

“The food is on its way,” she announced.

“It will take us a few minutes to clean all this up,” Carson said.

“No, don’t worry about that. Brian will take care of it later, just clean yourselves up if you need to. There are towels and stuff in that cabinet,” Fiona said, probably pointing at the cabinet, “and don’t bother getting dressed right now, I’ll get a couple of robes. Just untie Brian and come back to the living room.”

They brought my legs down but not fully together and then returned the chair to the upright position.

“Taste his cum,” Brandy said, “tell me how he compares to some of the others.”

I expected to feel a swipe across my chastity cage, but instead, Carson placed his hands on my thighs and began licking my balls and the cage! I squirmed and let out a tiny squeal but couldn’t get away. I was so sensitive after my massive orgasm, but I could also feel another one building and then I exploded again when Brandy pulled the nipple clamps off (I had almost forgotten about them) and roughly massaged my nipples. It’s always worse when they come off and I howled as Carson licked and sucked at my caged cock licking up the fresh cum as it flowed out in spurts.

“Don’t swallow that, give it to him,” Brandy commanded.

Carson pushed himself up to stand between my legs and leaned forward, placing his lips against mine. I had never kissed a man before and his short beard and mustache ticked my smooth face as I parted my lips. His tongue pushed past my lips as he fed me several large globs of my cum. As his tongue withdrew I sucked it clean and then followed it back into his mouth, where we intertwined again for a moment before finally breaking our french kiss. I couldn’t see his face, but I could feel his warm breath on my face as he lingered for just a moment afterward.

They began by removing the ropes from my body and then the chords holding my arms. I stretched to get the blood flowing again while they untied the chords that had been holding my feet and undid the straps across my legs. The soles of my feet stung and the muscles ached as I flexed each foot and wiggled my toes, but it was nothing like the ache in my well-used ass. I stretched one leg and then the other. The back of my legs and my ass burned from the thrashing I had received and I was sitting in a puddle of gooey lube that was draining out of my gaping ass. 

Since I was essentially free now and I could hear them rustling around doing other things, I reached up and removed the blindfold and rubbed my eyes, then opened them just in time to see Brandy’s naked ass as she walked out of the room. My eyes were still adjusting to the light, but she looked as good as had I imagined. 

I looked over at Carson and was shocked to see that he was wearing stockings with a garter belt and a lacy bra, all in black, and nothing else. His cock hung limply over his balls and his pubic area was shaved completely bare, unlike the last two times I had seen it. When he saw my expression, he laughed and picked up a pair of matching panties.

“She likes to make me dress up for her sometimes when we do stuff,” he explained as he stepped into the panties and slid them up his legs, tucking his penis and balls into the front pouch. “Usually it’s just our little secret, but Fiona knows that she makes me cross-dress and now you know my secret as well. I hope I can trust you or I’ll have to kill you”

He looked serious for a second and then he smiled.

“Don’t worry, your secret is safe with me,” I said and we both laughed.

When I finally slid off of the seat and put my weight on my feet and groaned as I felt the pain from the welts.

“Just take your time, you’ve got this,” Carson said catching my arm. “She loves doing the feet. She says it is a good reminder for a sub.”

“I’m not going to forget this anytime soon,” I said, regaining my composure.

“Put some lotion on them when you go to bed and also on the back of your legs. She gave you some serious color back there,” Carson said, examining my backside, “but she really is an expert. She didn’t break the skin even once and you’ll be surprised how quickly they fade.”

“That was the most intense session I have ever experienced,” I said as I looked around at all of the stuff I was going to be cleaning up later. I spotted the strap–on harness with the massive dildo that had so recently been pegging me. It was one of Fiona’s largest and, as far as I knew, it had never been used before today.

“You took that thing like a champ,” Carson said, noticing where I was looking. “It was so fucking hot to watch your ass getting stretched. I even made a video. I’ll send it to you later if you want to see it.”

“I thought I heard your phone,” I said. “Please, do send it to me. Fiona likes to record us doing new things and she even makes me post them online sometimes.”

“Really? And how do you feel about putting yourself out there like that?” Carson asked.

“It’s extremely embarrassing, especially reading all of the comments and watching the view counter climb and knowing how many people have seen me naked or doing things,” I said, blushing again just thinking about it.

“Maybe she’ll let you post the video of you getting impaled by that monster cock,” Carson jibed.

“Right, ‘let me”, more like ‘make me’,” I laughed as I limped out of the room with Carson at my side.

I was almost walking normally when we reached the main part of the loft. Brandy was already back on the sofa wearing a short purple silk robe and sipping wine. Fiona was sitting next to her and was just filling herself a glass.

“I left you the pink one to go with your outfit,” Brandy teased nodding towards a similar pink robe. “Don’t bother with the tie, just let it hang open.”

Carson put on the pink robe and left it open as instructed before sitting on the loveseat across from his wife with his legs spread open just like I had been taught by Fiona.

“I had better go get a quick shower,” I said as I felt another stream of goo from my ass run down my inner thigh.

“Don’t you dare,” Brandy snapped and then looked at Fiona. “Sorry, he’s yours, I didn’t mean to overstep but didn’t you say the food would be here soon?”

“Yes, the app said it was out for delivery 10 minutes ago and they are only about 10 minutes away so any minute.”

“I think he should be proud to wear Carson’s cum on his face and feel the fluids leaking down his legs, don’t you?” Brandy asked.

Fiona looked at me and I could tell from her expression that she was going to side with Brandy on this. 

“It will be alright. If it’s the usual delivery guy, Akeno, he’s already seen you naked several times,” Finoa said, “You are just a little more…disheveled this time.”

A little disheveled was an understatement!  But I knew better than to argue, especially since my ass was already raw.

“Yes, ma’am,” I said, looking into her beautiful green eyes. I would do anything for her.

She mouthed a kiss and, right on que, there was a knock at the door.

I straightened my back and resigned myself to doing this as I marched over to the door on my sore feet and opened it, not trying to hide myself in the least.

Akeno was a young skinny Asian guy, probably only 18 or 19. His hair was black with an electric blue stripe from front to back on one side. He was clean-shaven (or didn’t grow facial hair yet) and he was wearing blue track pants and a black t-shirt with the restaurant logo on it. He was probably at least a second-generation American so he didn’t have an accent except for the skater vernacular that he liked to use. 

“Hey, Brian, I’ve got your….” Akeno stopped short as he caught sight of Brian.  “Are you okay, dude?  You look a little rough today.”

“Yes, I’m fine,” I laughed, “we’ve just been having some fun with our friends.”

Akeno looked past me at Fiona, with Brandy and Carson in their silk robes, sitting in the living room, then back at me. 

“Looks like it was quite a party,” Akeno said as he grinned and winked. “Maybe next time you’ll invite me.”

Akeno started handing me containers of food from his warming bag. Once my hands were full I turned to take them to the kitchen. There were so many that I was going to have to make two trips.

“Damn, dude! Did you piss somebody off?” Akeno asked as he got a good look at my bright red ass and red striped legs.

Brandy was whispering something in Fiona’s ear and as I was placing the food containers on the kitchen bar, she got up and went to the door.

“Akeno, why don’t you go ahead and take the rest of those to the kitchen,” she said.

“Okay, Miss Fiona,” he said. He had always called her that ever since he started delivering to us.

Akeno followed the same path around behind the sofa that I had taken and started pulling out the remaining containers as I arranged them on the bar.

“Thank you,” I said as he was folding up the empty bag.

“Brian, don’t you think he deserves a special tip for delivering such a large amount of food this time?” Fiona asked, sounding a little coy.

“Uh, sure,” I said a little confused and not taking the hint.

“Akeno, would you like Brian to suck your cock?” Fiona asked bluntly.

Akeno smiled and looked around.

“Is this for real? Are you guys doing one of those hidden camera shows or something?” Akeno asked.

“No hidden cameras, he really will if you want,” Fiona said, moving over next to me.

Akeno thought about it for a minute and glanced around again.

“Well, I won’t ever say no to a blow job,” Akeno said

I groaned inwardly as I sank to my knees in front of this young asian guy. I can only imagine how I looked to him with cum drying in my hair and on my face and rivulets of cum and lube and whatever else running down my legs, but he was just smiling and looking eager for his blowjob.

I hooked my fingers on the waistband of his track pants and pushed them down to his feet. He was wearing blue boxers underneath and I could see the bulge where he was already starting to rise to the occasion. I slid his boxers down next exposing his cock. It was about what I expected, average-sized and surrounded by thick dark hair. As it got harder, it was pointing straight out in front and bobbing a little from his excitement.

He had a musky smell that wasn’t bad, just different. I took his cock  between my fingers with one hand and guided it into my mouth. I had never sucked a cock with this much pubic hair before and it ticked my nose when I took his full length. I fondled his balls with one hand and reached around to grab his ass with the other and hold him steady while I bobbed from base to tip, pausing occasionally to tease his glans. I was doing everything I could to get him off as quickly as possible.

“Fuck, dude, you really know how to suck a cock,” He said, moaning. “ You’re better than my girlfriend!”

“He gets a lot of practice,” Fiona said, making me blush again. 

She was just standing there next to me watching me suck this guy off in our living room. Brandy and Carson also had a good view from where they were sitting. Fiona had probably planned it that way and that was why she had asked him to come in.

“I can tell,” Akeno said, still moaning softly.

I was just thinking that it was a surprise how long he was holding when he pushed his hips forward and grabbed my head, holding me all the way down on his cock. I had no trouble taking it, it barely reached the back of my throat.

“Fuck! I’m going to cum!” he yelled.

I sucked hard and flicked my tongue around his shaft as he started to spasm and fill my mouth with his warm creamy load. When he had finished, I made a show of swallowing it and then I licked his cock clean and finally licked my lips.

“Thank you for your delicious cum, Sir,” I said, the way Fiona had taught me to thank my friends.

Akeno just stood there coming down from his climax for a minute before bending over and pulling up his boxers and then his pants.

“That was amazing!” Akeno said. “You see that kind of stuff on the internet but you never believe it can happen in real life.”

He was looking at Fiona and not me, almost as if he was embarrassed about what he had just done.

“Brian just loves the taste of cum, don’t you?” Fiona said, drawing the attention back to me.

“Yes, ma’am,” I said, blushing again at the admission. 

“Well, if he likes Asian, he can have me anytime,” Akeno said, laughing as he picked up his bag.

“I hope you will keep this to yourself,” Fiona said as she walked him to the door. “If you do, maybe this can be a regular thing whenever you deliver.”

“That would be cool!” Akeno said excitedly, “And I won’t tell anyone. They wouldn’t believe me anyway.”

As he left, I got up off of my knees and grimaced as I put my weight back on my sore feet, then went around to the kitchen cabinets and pulled out plates and silverware and such as everyone came over to get the food. It smelled so good my stomach growled.

“Brian, why don’t you go and get that shower now,” Fiona said quietly when she returned to the kitchen.

“Yes, ma’am,” I said. “Thank you…for everything.”

She kissed the back of my neck, probably the only spot that wasn’t coated in some kind of drying fluid.

I headed off to the bathroom as Fiona and Brandy got up to make a plate for themselves. The warm water felt good on my head and face but it stung a little at first when it hit my ass and legs. Even the soft towel I dried off with felt like 80-grit sandpaper on the backs of my legs.

I rejoined the party after I had finished drying off, brushed my hair, and spritzed a little cologne. The others were sitting in the living room with half-eaten plates. I filled a plate for myself and joined them.

“You were quite impressive today,” Carson said shortly after I sat down.

“Yes, he is quite exceptional,” Brandy said, more to Fiona than me.

I glanced at her and saw that her robe had fallen open slightly giving me just a hint of the bare flesh underneath. 

“And don’t worry about that delivery guy. It will all work out,” Carson said, breaking my spell.

“It will be like Aldo,” Brandy said.

“Yes, exactly!” Carson said, then explained, “Aldo was the delivery guy from the Italian place we like. Brandy made me do pretty much the same thing you did today and I would have to do it again every time he delivered. He’s the manager there now but if he sees an order from us come through, he will still make the delivery sometimes and get his cock sucked.”

Everyone laughed, including me, though I was less amused at the thought of sucking Akeno’s cock for the next 20 years.

“He and his wife, Myra, even joined our House. She’s got great tits and a very spankable ass so we were happy to have them,” Carson said and we all laughed again.

“So, this could be the start of you building your own House,” Brandy said, looking at her plate and avoiding Fiona’s gaze.

Brandy had been pushing Fiona to start building her House for a while now. It wasn’t a sore subject or anything but Fiona wanted to do it in her own time. From what I understood, a House was a group of people who were into all this BDSM stuff and did stuff together under the leadership of a stronger more experienced Dom or Domme. Each House was also part of a larger Community. Each house had its own rules and ways of doing things but they all had to conform to the Community standards and there were lots of formalities and social events that would put a lot of pressure on Fiona. But Fiona had explained that, as Brandy’s protege, it was expected that she would establish her own House, otherwise it might affect Brandy and her House’s standing in the Community.

“I promise, I am working on it,” Fiona said, “I was going to ask if you could arrange a meeting with the Community leaders sometime soon so I could so I could make it official.

“Of course!” Brandy said, her face lighting up, and put a hand on Fiona’s knee. ”I’m so happy for you.”

“Have you decided on a name? You will need that when you talk to them. You should also have at least 5 or 6 people lined up,” Brandy said.

“I have some ideas, I’ll be ready,” Fiona said.

The conversation shifted around to various other topics after that and continued to sample different dishes. I kept wine and water glasses filled and when everyone decided that they couldn’t eat another bite, I took all the dishes to the kitchen.

“It’s getting pretty late,” Carson said, looking at the clock on the wall. “We should probably get dressed and head home, don’t you think?”

“Yes, but first, your sub owes me a favor,” Brandy said with a wicked grin. “He promised to do anything.”

“Oh, did he now?” Fiona said with mock surprise. “What did you have in mind?”

“Well, I was having a great time fucking his cute little ass when he begged me to stop after he had his little orgasm – without permission, I might add,” Brandy said, smiling playfully.

“Really? Brian, I taught you better than that!” Fiona exclaimed with over-the-top outrage, putting her hands on her hips.

“I…I’m sorry,” I stammered, not knowing what else to say, “It just came on so fast that I didn’t have time to…”

“We don’t want to hear your excuses,” Brandy said, cutting him off. “But I told you I would take you up on your offer later. It’s later.”

“Yes, ma’am,” I said, looking down at the floor.

“Has your old sissy cock recovered sufficiently to fuck me?” Brandy asked Carson.

The look on his face made Brandy and Fiona giggle.

“I think I can handle your old worn-out cunt,” Carson said, smiling.

“Oh, honey, you really know how to sweet-talk a lady,” Brandy replied, laughing. 

“Get that robe off and let Brian get you hard for me,” Brandy ordered.

“Yes, ma’am,” Carson said. 

He slipped the robe off his shoulders and left it on his seat, then approached me where I was standing next to Fiona. I lowered myself onto my knees for the second time this evening.

“Just pull the front of his panties down enough to take his cock out,” Brandy directed.

I pulled the black lace down releasing his half-hard member and leaving the panties to cup his balls. I caressed them through the lace as I licked and kissed the head of his cock. He tilted his head back and sucked in a breath. He was already growing and I love feeling a cock go from soft to hard in my mouth so I didn’t waste any more time. 

I used my tongue to lift his cock to my lips and sucked just the head in and closed around it. I flicked the tip of my tongue into the little slit and then swirled it around and teased the glans.

“Oh god, you are such a cock tease, Brian,” Carson said looking down into my eyes.

I teased him for another moment and then parted my lips and pushed slowly forward until my chin was against the lacy panties and his cock was in my throat. I worked his shaft in and out a few times, sucking hard enough to make rude noises, until he was completely hard.

“That’s enough, save some for me,” Brandy said. “Get your ass over here and lick me.”

Brandy had opened her robe and was sitting on the loveseat caressing her breasts. She spread her long slender legs and I looked from her to Fiona, who was in the armchair where she could watch everything that was going on. Fiona just smiled and nodded toward Brandy. 

I crawled away from Carson and between Brandy’s legs. My earlier question was now answered: she was shaved completely bare. She barely had any scent at all, just a hint of coconut or some exotic flower, probably from her soap or lotion. Her inner labia were slightly elongated and she had a large protruding clit. I could see that she was already moist even before I leaned in and gently slid my tongue from the bottom of her slit to the top. When I bumped against her nub, she flinched. I did this a few more times, pushing my tongue deeper and deeper between the labia and they seemed to part as she became more aroused. On my last trip to the top, I kept going and raked the whole length of my tongue over her clit.

“Oooh, yes, right there,” she crooned.

With her encouragement, I focused my attention more on her clit. It was long enough that I could suck it between my lips and gently nibble on it. That seemed to drive her crazy and finally, she put her hand on the back of my head and smashed my face against her as she shook and moaned with her first orgasm of the evening.

As her wave subsided she pushed away and told me to turn around and she got up, removed the robe, and tossed it aside. Then she straddled with her legs wide and bent over at the waist, putting her hands on the back of the loveseat so her ass was facing Carson and Fiona and her tits were swinging freely above me. She still had an amazing body. Not as good as Fiona’s but, especially for her age, it was fantastic.

Facing this direction I could also see Fiona and Carson. Fiona had taken her pants off and was stroking her pussy with one hand while she fondled Carson’s cock and balls with the other, keeping him hard.

“Get over here, you big sissy,” Brandy called to her husband.

“I thought you would never ask,” Carson said as he pulled away from Fiona and approached Brandy with his cock bobbing in front of him.

I had an up close and personal view as he rubbed his cock against her slit a few times to get it lubricated before ramming it into her. 

“Unngh, that’s it, fuck me, sissy,” Brandy grunted. “And you, slut, don’t just sit there staring, it’s not going to lick itself.”

I raised up and started licking her pussy and clit as well as Carson’s cock as it plunged in and out of her wet hole. I had never done anything like this before and my cock was raging in its cage. It wasn’t long before the combination of my and Carson’s efforts brought Brandy to another shuddering orgasm. 

“Keep at it, Brian,” Carson said, “Push her through to the next one.”

I redoubled my efforts on her love button as she screamed and moaned loudly and Carson seemed to do the same with his thrusts. Just as she seemed to be coming down from the last orgasm, her next one rocked through her while Carson and I just kept going.

Watching her tits flailing during the throes of her passion gave me an idea. I reached up with one hand and grabbed her breast and started rolling her nipple between my fingers while I continued to lick and suck at her clit. This set her off again and she was bucking so much I had to let go in order to keep up with the movements of her hips. She was pushing back to meet Carson’s thrusts and driving his cock as deep as it would go.

“I’m going to cum if you keep that up,” Carson said after holding out as long as he could.

“Cum for me, baby. Fill my cunt full,” Brandy said huskily, “And you be ready, slut. When he pulls out, you are going to clean every drop of cum out of me and I don’t want you to miss a drop.”

“Yes, ma’am,” I said and positioned myself below them with my mouth open.

“Oh, fuck, I’m cumming,” Carson said and they both paused and I watched his balls contract and his cock throb as it pumped his load into her pussy. 

When he stopped pulsing, he slowly pulled out and smeared the last drops of his semen across her clit. As he stepped back, Brandy lowered her gaping cunt to my face and pressed my lips to hers, and started to lick and suck. Gobs of creamy fluid flooded my mouth and I swallowed several times but kept licking until she grabbed my head with both hands and rode my face as she had her final orgasm. 

When she released me, I gave her clit a gentle kiss before she took a step back. My face was covered in hers and Carson’s cum but I was smiling. I had eaten my own cum out of Fiona’s pussy many times but I had never eaten another man’s creampie before — and out of another woman’s pussy! 

I looked over at Fiona and she looked a bit rumpled like she had brought herself to orgasm at least once, probably more, while watching us. She caught me looking and smiled and gave me a wink.

“You guys were hot,” Fiona said, sitting back up in the chair, still naked from the waist down.

Brandy, still completely nude, sat down on the sofa next to Carson and just kinda melted into the seat.

“That was really good, I think you got your money’s worth out of Brian,” Carson said to her.

“He eats pussy as well as he sucks cock. You should be proud of your little slut,” Brandy told Fiona.

“Yes, he is a good boy,” Fiona said looking proudly at me.

I just smiled and laid back on the loveseat, exhausted.