Fiona and Brian Chapter 4 — Big Mistake

At this point, it had been several months since I finally gave in to her bi training. She made sure that I was only allowed to cum when I was sucking another man’s dick. She especially liked to time my own orgasm to coincide with his, and after swallowing his load, I was fed my own cum as well. I had to admit that I had mostly gotten over any hesitation and was finding myself thinking about ways to improve my technique, and sometimes (especially after a long denial), I would imagine the feeling of a cock slipping into my mouth, and I would crave the taste of the semen that would soon follow.

Between orgasms, I was kept very aroused, pleasuring Fiona, being teased by her, and masturbating to the edge while she watched. Recently, she hadn’t been allowing me to cum even if we had a session with me sucking a cock. The frequent humiliations with our friends also kept me very concupiscent, and Fiona would occasionally allow her friends to touch and examine me in some intimate and embarrassing way. She would always tell me before they arrived that she wanted me to stay as hard as possible while they were there. I was expected to stand, not sit, and always face her and our guests so that I would be on full display unless directed otherwise. Sometimes she would absentmindedly fondle my scrotum or lightly touch my erection as I stood beside her, never pausing the conversation but definitely breaking my concentration.

Fiona had also increased the amount of bondage and spanking during our lovemaking, and she had started adding some new things like cock rings and leather straps that stretched and separated my balls. Devilish nipple clamps came next, and her latest new toy was an anal hook with a huge round ball on the end. It was amazing how humiliating being tethered to the wall or led around on a leash by my own ass could be, and also how hard it could keep my cock.

I loved Fiona so much and in so many ways, and I enjoyed everything we did together, but the constant teasing and denial eventually started to wear on me. I was right on the edge constantly, I could barely think about anything except the next time I would get to cum. I was living for the next time she would stroke me or let me masturbate, even though I knew it would only leave me more frustrated. I woke her up by crawling between her legs and licking her pussy most mornings, and I waited impatiently for her to get home from work so I could give her another round of orgasms, then again in the evenings before bed, I would do it again. I dreamed about having a fat cock filling my mouth with cum so that I could finally have my own release. Still, the last three times I had serviced my anonymous friends, she had only said “Not this time, my pet,” while she fed me the drops of precum that she cleaned gently from the tiny hole of my sensitive penis.

So it was, while she was out working at the art gallery one day, that I broke one of the cardinal rules – I opened an incognito browser window, and browsed to one of my favorite porn sites that I used when Fiona wanted me to edge. I told myself I just needed to masturbate for a moment, only this time, Fiona wasn’t there to make me stop. I didn’t make it two minutes before I exploded! It felt so good to release that I screamed out loud. I didn’t think the cum would ever stop. Even though I was too sensitive to continue stroking myself, I continued to convulse and squirt with my fist wrapped around my shaft. When I was finally spent, I fell back into my chair. I might have even blacked out for a minute.

After I had recovered, I was appalled by what I had just done. I immediately went into cleanup mode. I was ashamed, and I knew Fiona would be…what? Angry? Disappointed? I had never broken this rule. I had never really broken any of the rules she gave me because I only ever wanted to please her. She had “punished” me for little transgressions before, but mostly just for fun, but now I had done THIS, and I couldn’t bear to think about her finding out. Oh, god, there was even cum on the monitor, and the keyboard…and the chair! I could even smell the unmistakable scent of semen. I furiously cleaned everything. Cleaning was one of my chores around the house, so at least that wouldn’t be suspicious. If she noticed anything, I could just say I spilled something on my desk and had to clean it up.

Finally, I felt like I had erased every trace of my transgression, and I put away the cleaning supplies and sat down to have a beer before Fiona got home. That’s when it hit me – I wasn’t hard! Fiona would notice that I wasn’t on the edge anymore. How could I be so stupid? So, back to the computer I went and opened the porn site. It didn’t take me long to find my edge again. I stroked and then stopped for a minute, then stroked some more. I closed everything down when Fiona texted me saying she was on her way home. I hoped I was horny enough again.

When I greeted her at the door, she asked, “Hello, Pet. How was your day?”

“Um, not bad,” I said.

“Not bad?” she asked with an impish grin as she grabbed my shaft tightly. “Did you miss me?”

“Oh, yes, very much,” I replied, swelling in her warm, soft hand.

“You have been such a good boy lately,” she said, releasing my penis and cupping my sack instead. “How long has it been since you had a good orgasm? Maybe we can invite a friend over this weekend.”

“Mmm,” I moaned, “I would like that very much.”

It seemed that I had gotten away with my transgression, and now I was definitely excited at the prospect of getting to suck off one of my friends this weekend.

Saturday evening, Fiona told me to go to The Room and get in the chair. I was so excited I practically ran. Seeing the old medical chair I had installed for her made me shiver as I climbed into it, locked my legs into the stirrups, and fastened the straps around my hips and chest. I put on the leather blindfold that still kept me from discovering which of my friends knew firsthand that I was now an eager cock sucker. Finally, I settled back to wait for Fiona to do the rest. It must have been 15 minutes before the door opened. My cock bobbed as I heard Fiona’s heels clicking on the hardwood floor.

“My, my, you are eager tonight, aren’t you, Pet?” she said as she fastened leather cuffs on my wrists and attached them to metal rings on the edge of the chair by my sides, then checked the tightness of the other straps.

“Yes, ma’am,” I said, my voice cracking a little.

“Are you excited to suck cock this evening?” she asked sweetly, teasing the tips of her fingernails across my bare chest.

“Yes, please. I need cum,” I said, using the words that had only recently started coming so easily from my lips.

“I’ll bet you do, my pet…especially since you wasted so much of your own earlier this week,” she said, her voice taking on a hard edge.

I gasped, momentarily speechless, then I started to plead, “Oh god, I’m so sorry, Fiona, I don’t…”

“Shhhh,” she said, putting her finger against my lips, “No more words. You don’t need to explain. I know it was a long wait for you this time, but you broke one of the most important rules. So, tonight I will punish you, and afterwards, I trust you will never break it again.”

I was terrified. Fiona had never sounded like this before, and as I said before, she had never punished me for any real transgression, so I had no idea what to expect. My mind raced with the possibilities as I lay helpless and totally exposed in this wicked chair.

She moved to the controls on the side so the chair tilted back fully horizontal, then walked around to the top and lowered the headrest so my head could fall backward, ready to accept a cock into my open mouth. She then placed a strap across my forehead and bound it to the headrest, which forced me back even farther and kept me from being able to move my head in any direction. Next was something new for me. She forced a metal ring into my mouth behind my teeth. It had some kind of ratcheting mechanism that allowed her to spread it farther and farther, forcing my mouth to open wider and wider until I started to panic and pull at the cuffs on my wrists.

“Just relax, I promise, this won’t hurt…too much. I would never do anything to injure my favorite pet, now would I?” she purred.

I was terrified, but I knew that I could trust Fiona above all else. Safe and sane was one of her favorite catch phrases. Her voice was softer than before, and I relaxed as much as possible in my current state. My cock was standing tall, so she knew I was still more aroused than afraid.

She moved around to the other end of the chair and raised and spread my legs as far up and apart as they would go. I knew every square inch of my most private parts were completely on display now, and she proved it by pulling out my plug, and not gently. She then slathered a cold gel all over my cock and balls and even worked it into my gaping ass hole. It quickly changed to a warming tingling sensation that made me squirm.

“Be still,” she said as she slapped my ass cheek hard.

I stopped squirming as the cream continued to work on me. It felt like something with a million little legs was crawling all over my cock and balls, making them itch and tingle, and I kept clenching my asshole trying to satisfy the maddening sensations I could feel from the outside rim down past the inner sphincter.

Next came the clamps on my nipples — how I hated those things. From the feeling, it was the butterfly clamps. They always hurt the most and seemed to tighten if I struggled against them even a little. Speaking of which, Fional pulled the chain between the two clamps taut and attached it to one of the hooks in the ceiling, so every movement tugged painfully on my nipples.

I heard the door open and then close, followed by bare feet on the floor. I assumed one of my cum buddies had joined us. It occurred to me that this was the first time my hearing wasn’t blocked by noise-canceling earbuds. Maybe this would be my chance to identify one of them.

I could smell his scent as he moved closer to my face. Then I felt his cock enter my mouth, and the head touched my tongue. My mouth was so wide that it only brushed against my lips. Normally, I would close my mouth around the shaft and suck, but that was impossible now. I flicked my tongue and felt the cock flinch, but it never stopped its forward motion until his balls were pressed against my nose as he forced his way into my throat. It was the long cock. I could only take a breath and swallow as I fought against my gag reflex.

Suddenly, a new sensation grabbed my attention – pressure at my anus, something forcing its way inside. It felt like an enormous dildo. It entered me slowly, and I thought it was never going to end. Inch after inch, or maybe foot after foot, crawled past my sphincters. Finally, I felt Fiona’s thighs press against my bare buttocks as the last of it slithered into me like a giant snake.

“Do you like my new toy?” She asked, “Oh, sorry, I see your mouth is full right now. Don’t worry, I think we will be using this a lot more in the future. I like being able to fuck you the way that you fuck me. Only, mine is a bit larger than yours,” she chuckled.

I moaned around the cock that was starting to grow larger as I choked on it, causing drool to stream out of the corners of my mouth and run down my face towards the top of my head.

“Fuck his mouth,” Fiona said, almost a growl, “while I take his ass.”

In unison, they both started to move. The strap-on pulled almost completely out before plunging back in until her pelvis slammed against me. My cries were almost completely muted as the cock in my mouth withdrew and then plunged back in again, with force this time, his balls slapping against my face. They continued and started to get into a rhythm, pushing and pulling, rocking me just enough between them that the clamps were constantly tugging at my nipples, making them ache horribly. The long rod in my ass was filling me with every thrust and emptying me with every withdrawal, and I could feel the precum oozing from the tip of my penis as it danced rudely in the open air.

Meanwhile, I had passed through the gagging stage, and now I was just taking the cock down my throat like a professional whore. I was trying to use my tongue to tease his cock and speed up his orgasm, but with my mouth stretched so wide and his sensitive head down in my throat, there wasn’t much I could do.

There wasn’t anything I could do about any of it. I was just a couple of holes being used at this point. I felt bad because I had let Fiona down, and now I was being raped in both my holes as punishment, but it was better than I deserved. I just wanted it to be over so I could beg her to forgive me and find a way to make it up to her. I was slipping into that zone of acceptance. I knew I wasn’t supposed to enjoy this, but I couldn’t help but feel pleasure along with the pain and degradation.

After what seemed like hours but was probably only a few minutes, I felt my friend start to slow his pace, and his cock grew just a bit bigger. I knew he was about to cum, so I doubled my efforts trying to add additional stimulation with my tongue. After a few more strokes, he pulled back and emptied his load into my mouth. It was difficult to swallow in my current position, but I did my best, though most of his cum dribbled out of my mouth and across my upside-down face, getting into my nose and hair. Thankfully, the blindfold kept it out of my eyes for now.

Fiona slowed her pace as well and let the long phallus pop out of my sore ass. I could still feel the maddening tingling sensation on my cock and balls now that the other stimulation had subsided. I desperately needed to scratch and rub my balls. It’s like a guy’s worst nightmare to have an itch there that you cannot scratch. Just as I thought we were finished and she might release my hands, I heard the door open and close again and more bare feet shuffling on the floor. I was confused by what I was hearing until Fiona spoke.

“Ok, boys, we’ve loosened him up for you. Now it’s your turn,” she said.

I was in shock, but before I could even try to speak, there was a fresh cock being pressed into my mouth. This one wasn’t fully hard yet, but it started growing quickly as I swirled my tongue around the head and shaft. It was the regular-sized guy. At the same time, I felt someone standing between my spread legs. A warm, hard cock was pressed firmly into my freshly pegged anus. I grunted as my sphincter strained to accommodate his girth.

Since I already knew the other two, this had to be the thick cock getting ready to stretch my hole. I was going to be fucked by another man for the first time in my life! I was mortified knowing that three of my friends were taking part. How could I ever look any of my friends in the eye again after this?

I tried to protest, but all I could manage was a hum as the cock in my mouth swelled and started to grow slowly past my tongue, while the cock in my ass filled me completely, and I felt his balls slap against me before he started pulling out for another stroke. Soon, they had me bouncing back and forth between them. I could feel the clamps tightening on my nipples as the motion pulled on the chain. Jolts of pain and pleasure rippled through me from so many places that my mind couldn’t process them separately.

“Are you enjoying your first real spitroast, my naughty pet? Do you think you will be able to follow the rules after this?” Fiona crooned into my ear, reminding me why this was happening.

Shortly after that, yet another sensation startled me as she wrapped her hand around my straining member. It was so incredibly sensitive! Whatever that tingling stuff was that she had used, it had kept me hard this whole time and also made her slightest touch an exquisite sensation. She hadn’t told me I could cum, but I knew I couldn’t hold out long like this. Just as I reached my climax, she let go. I was too far gone, and I moaned as my semen spurted for the longest time. It was a release, but completely unsatisfying. She had ruined my orgasms in the past, but never when I needed one as badly as I did now. The cock drilling into my ass was hitting my prostate perfectly. Thanks to whatever this stuff was she has put on me, I could feel every single inch of his shaft as his fat cock pistoned in and out of my tight hole. Now that I had had my first taste of cum, I craved more and thought about my own cum being wasted. My cock and balls still itched and tingled. My nipples were on fire.

I was starting to get hard again, and Fiona began working my growing member in her hand to help it along. It wasn’t more than a minute before I felt another orgasm building, but the cock in my mouth beat me to it. I still couldn’t swallow much, and this guy must have been saving up all week because he flooded my mouth, and it just ran down my face. He smeared the last few drops across my chin as he stepped away. Normally, I would suckle the last few drops while I cleaned my buddy’s shaft, but this time I felt like I missed my prize. Was I actually upset that I missed a few drops of cum? What had I become?

Fiona’s ministrations paid off as my second orgasm started, and she immediately stopped again, letting the cream just trickle out this time, but she picked this moment to snatch the clamps off of my nipples.

“Oh, holy fuck!” I yelled as the blood rushed back into the tortured nubs, but with the spreader in my mouth and all the cum, it just came out as unintelligible gargle.

Fiona grabbed them both and started kneading them between her fingers.

“Son of a bitch!” I tried to yell again, squirming but not able to get away.

She didn’t stop, but the guy pounding my ass erupted inside of me. I could feel him shoot hot, thick semen deep into me as he forced his pulsing cock as deep as it would go. When his orgasm finally subsided, he slowly pulled out and walked around to my head.

“Clean it up and thank him for taking your anal cherry, slut”, Fiona commanded.

I could smell my own ass on his shaft, but I licked as best I could with the gag.

“Push the cum out of your ass,” Fiona said as I continued to flail my tongue around my friend’s cock.

I pushed, and both heard and felt the slimy mess bubble and ooze out of my tender hole. She used her finger to dig out a final glob.

“Raise him up,” Fiona commanded, and the guys worked the mechanism to tilt the chair back upright and released the strap holding my head back. My neck was stiff from getting face fucked in that position.

The spreader in my mouth was screwed back down and finally removed. My jaws ached, but I still took the opportunity to lick the cum off my lips before doing anything else. I could feel the gooey mask on my face sliding back down.

“I know you didn’t get to drink most of their cum this time, but you will drink every drop of this cum that came out of your ass,” Fiona said

I started to say, “Yes, Ma’am,” but a glass was pressed to my lips before I could even begin. I tilted my head back as she raised the glass, and I both smelled and tasted the thick, salty-sweet flavor of semen mixed with something more musky. It wasn’t awful, but knowing where it came from made me want to gag a little. Still, I did as I was ordered without hesitation and quidrank it all quickly before I could think about it anymore.

“Good boy,” she said when the glass was empty. “You better get used to that taste, I think you will be drinking the cum from your ass more often now that you have been properly broken in, your friend seemed to like using your ass instead of your mouth, and we don’t want the others to be jealous.”

As I started to come down from the excitement, I heard the others still in the room. They had all stayed to watch my complete degradation, but I had been so distracted I didn’t remember hearing even a grunt or moan from any of them.

I heard the door open and everyone shuffle out of the room, followed by the click of Fiona’s heels. I was alone with my thoughts as I sat there, legs still spread like a gymnast, feeling a trail of cum leaking from my ass, and dripping off my chin onto my chest, where it trickled down to join the puddles of my own cum on my abdomen. At least whatever she had put on my cock and balls was finally wearing off. I wondered what else she had in store. I couldn’t imagine what might come next.

I didn’t have to wait too long before I heard the door open and close again, and I could hear Fiona’s heels again.

“Just one more thing, and then I’ll let you free to get cleaned up,” she said.

There was some metallic rattling, and she pushed my balls one at a time through a metal ring, followed by my mostly flaccid penis. She snugged this down, and then something cold and hard slipped over my cock, pressing it down even as it was starting to rise again. She attached something to the bottom of the ring that folded down, and a large metal ball similar to the anal hook was forced into my now gaping asshole. I groaned as it stretched my sore ass, but once it was in place, my sphincters closed around the shaft below the ball comfortably. I could tell from its girth that it wasn’t coming out easily. Finally, I could feel her connecting everything together, and then there was a “snick” as a small lock was closed.

At long last, she brought my legs back to a normal position, released my arms, and removed the blindfold. The cum was still creeping down my face. I quickly wiped it out of my eyes and then licked it off my fingers without even thinking about what I was doing.

“You have become such a little slut”, she giggled.

Looking down between my legs, I saw a shiny steel chastity cage. Fiona reached between my legs and toyed with it.

“Go and take a shower, you are a real mess,” she said. “Don’t dawdle. When you’re done, come back here and get into the shackles facing the wall.”

I showered quickly, getting the muck off of my face and out of my hair, then I washed my caged cock as best as I could to get the last of the tingling cream off of me. The cage was a series of rings that had been welded together, so there was plenty of access for the water to wash through, but the rings were close enough together to prevent any real contact from outside. I definitely wouldn’t be masturbating with this thing on.

The ring around the base was wider than the rings on the cage, which pushed my scrotum out away from my body so that my balls were put on display. At least I could finally scratch and rub them. My asshole was so raw I didn’t want to even attempt to remove the plug, so I just washed around it as best as I could. I could still feel that irritating cream inside me, but there wasn’t much I could do about it.

Once I was done and drying off, I checked out my new hardware in the mirror. The cage over my cock was only a couple of inches long; Fiona must have sized it to fit me at my smallest. Any erection was going to be interesting. The plug was attached to the bottom of the base ring, and it was hinged so I could be temporarily unplugged without removing anything else. She had really thought of everything.

I hurried back to The Room and walked to the far side, where I had attached steel chains to the wood plank walls with heavy eye bolts per her instructions. At the loose end of the chains were wide leather cuffs that locked closed with padlocks. The padlocks were open now, but she kept all the keys in a metal box on the opposite wall, and only she had the key to that, so, once the locks were closed, she was the only one who could open them. She had shortened the chains so that I had to spread my legs pretty wide to get both ankles into the cuffs. I had to stretch to pull the cuffs tight and then click the locks into place. The wrists were also shortened so that I had to stand on my toes and stretch my arms up and out. We had practiced this a few times before, so I knew I could do it, but it was a struggle. There was a small peg on the right side that would temporarily hold that cuff towards the center, so I would be able to reach it once the left was locked in place. I used my right hand to fasten the cuff around my left wrist and snap the lock into place. Then I had to work one-handed to get into the right cuff, contorting my hand around and using the peg to pull the leather strap and then jiggling the lock around through the clasp, finally pushing it against my wrist until I heard the last ominous click. Now I was spread-eagled with my face and caged cock pressed against the wall and my back exposed. I pretty much knew what was coming next.

I hung there for quite a while before she finally came in. I wasn’t wearing a blindfold this time, but I still couldn’t see her even with my face turned to one side.

“You have been a very bad boy this week. You broke one of the most important rules and had an orgasm without my permission. Then you tried to hide it from me,” she said, her voice hard again, as she paced behind me with her heels tapping on the wooden floor.

“I’m so sorry, I…” I started to say, but she cut me off again.

“Don’t speak to me again until we leave this room,” she growled.

I nodded, rubbing my face against the rough wood.

“You are going to find out what a cane feels like tonight,” she said, and I heard a soft swoosh as she swung the thin rod through the air behind me.

“I promise you won’t like it, and it is going to leave marks that will last for several days.”

Swoosh.

“If anyone asks you about the marks, you will tell them exactly what you did to deserve this punishment. Do you understand?”

I nodded again.

Her heels clicked on the floor again, and then swoosh, crack!

“Ahhh!” I cried out, unable to help myself.

Swoosh, crack!

I moaned, and not with pleasure. This was the most painful thing I think I had ever felt.

Swoosh, crack!

Tears were starting to form in my eyes. I couldn’t stop myself from reacting to every stroke. I don’t know how many she gave me. I never even thought to try counting after the shock of the first one, but my ass was on fire long before she stopped. I was sweating, and tears flowed freely down my cheeks. My already sore nipples were being rubbed raw against the wood, but the most incredible part was that my cock was straining against the cage!

I had lost all sense of anything except my stinging buttocks, so I was suddenly surprised when she dripped some cool lotion onto them and started to massage it into the welts. It burned a little at first, but soon made it feel a little better as the air gave it a cooling sensation. When my whole backside had been covered, I heard her snap the lid closed on the bottle. Then, she walked across the room and I heard the door open and then close.

I don’t know how long she left me hanging there alone on the wall. My buttocks ached, my asshole ached, my nipples ached, and the ball felt huge inside my ass. I tried to keep my nipples from touching the wall, but my arms and legs were feeling the strain of being stretched so wide for so long. On top of it all, my cock pushed against the cage. Fiona had given me several orgasms earlier, but they had all been ruined, leaving me almost as desperate as if I hadn’t climaxed at all. Now my cock wanted to grow again, but it couldn’t. I already hated this terrible thing.

Finally, Fiona returned. She unlocked the four locks and helped me down from the wall. My legs and arms felt like jelly. Once she was sure I was down safely, she left again, never saying a word.

After I had recovered a bit, I joined Fiona in the living room, sitting on the sofa beside her. My friends were long gone, of course, still leaving me to wonder which ones they were. She had changed out of the leather pants and corset she had been wearing in The Room and was wearing one of her long sleep shirts, looking very cute and girlish in stark contrast to her earlier demeanor.

“How did you know?” I asked, breaking the silence.

She smiled deviously and said, “I have my ways. You shouldn’t try to keep secrets from me. I still would have punished you if you had told me, but it wouldn’t have been as bad.”

“I won’t ever do anything like that again, I promise”, I said, lowering my gaze.

“I hope not. I prefer to have fun with you, not punish you,” she said, running her fingers through my hair. “I’ve told you, this relationship has to be based on trust. You have to trust me, and I have to trust you.”

She had told me that many times before, usually when she was about to introduce me to something new that I was hesitant to try.

“How long do I have to wear this?” I asked in a quiet voice, as I looked down.

She reached between my legs, fondled my balls lovingly, and said, “I’m not sure yet. Until I feel like I can trust you again, I suppose.”

Her touch sent electric waves through me. My cock immediately filled the cage.

Fiona smiled as she watched it strain against the metal rings, then she leaned back, sliding down to the edge of the sofa and spread her legs so that her shirt rode up, exposing her beautiful bare pussy. It glistened with clear liquid – she was clearly aroused. I didn’t need to be told what to do. I moved to the floor, kneeling between her gorgeous legs and buried my face in her cunt, lapping up every drop and working up to her sensitive little clit as my cock throbbed in its confined quarters.