The Room Pt. 03

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Caught masturbating without permission.
5.4k words
4.54
41.4k
30

Part 3 of the 3 part series

Updated 06/08/2023
Created 11/14/2016
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Time flies when you are having fun, or so they say. I my case it seemed to be standing still. It has been almost a month since Fiona has allowed me to have an orgasm, the longest denial period ever.

It had been months since she started keeping me nude at home and now it felt odd to think of wearing clothes all the time. They almost felt uncomfortable on the occasions when I was allowed to put something on. All of her friends and mine were now fully aware of the situation. Most of them got over the initial awkwardness soon enough. My friends mostly thought it was funny and made lots of jokes at my expense, especially when Fiona declared that nude was now my "default state" and I was to ask her for permission if I had to put on clothes of any kind. The guys just laughed their asses off the first time they heard me do that. Fiona's friends always wanted to know how they could get their husbands and boyfriends to be as accommodating as me. Fiona even invited my sister, Alicia, over for dinner on my birthday. I wasn't sure how that was going to play out but she just laughed after I explained why I was answering the door in my birthday suit.

"I shouldn't be surprised," Alicia said. "When you were a little kid, mom had the hardest time keeping clothes on you, do you remember that at all?"

Alicia was 5 years and a couple of months older than me so she had plenty of stories to tell about me as a kid and Fiona wanted to hear them all. I spent the night blushing profusely. Apparently she had encouraged my exhibitionist behavior on several occasions when she was supposed to be babysitting her little brother by allowing me to roam the house and even the back yard completely bare. The conversation brought back vague memories of running through the house naked being chased by my mom or my sister and I definitely remembered some of the events after I was a little older when I got into big trouble (like that time in the treehouse...) and only now realized how much she had been there egging me on.

"Too bad we couldn't have kept you plugged like that when you were little. I always hated wiping your ass," my sister joked after telling us one of her more embarrassing stories that had me blushing.

Wearing a butt plug 24/7 was the other thing that Fiona had required even before she started keeping me nude. That was something that I didn't think I would ever really get used to, and maybe that was the point. It had become more and more comfortable over time, but the plug she preferred that I wear most of the time was largish and made of stainless steel so it was heavy and made me feel very full. It was a constant reminder of the things I was willing to do for Fiona.

As you know, if you read my previous stories, it had also 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 mans 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 craved 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 facing 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 breaking the conversation but definitely breaking my concentration.

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

I loved Fiona so much and in so many ways I enjoyed everything we did together, but the constant teasing and denial did eventually start 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 every morning and I waited impatiently in the evenings to do it again. I dreamed about having a fat cock filling my mouth with cum so that I could finally have my own release, but the last three times I had serviced my anonymous friends, she had only said "Not this time, my pet." while she fed me the few 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 I 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! I screamed out loud, it felt so good to release. I didn't think the cum would ever stop. Even though I was too was 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 smell the unmistakable scent of semen. I furiously cleaned everything. Cleaning was one of my chores around the house so that wouldn't be suspicious. If she noticed anything I could just say I spilled something by 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. When Fiona sent me a text saying she was on her way home, I closed everything down. I hoped I was horny enough again.

"Hey, Pet, how was your day," she asked when I greeted her at the door.

"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. The sight of the old medical chair I had installed for her months ago 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 three friends knew I was now such an eager cock sucker, and then 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 hard wood 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, maam," 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, he 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 that you will never break it again."

I was literally terrified. She had never sounded like this before. Like I said before, she had never punished me for any real transgression. I had no idea what to expect and 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 backwards, 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 wanted to scream but I knew that I could trust Fiona. Her voice was a little softer than before and I relaxed as much as I could 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 now and both 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 my 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 then 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, she had used the butterfly clamps. They always hurt the most and they seemed to tighten if I struggled against them even a little. The chain between the two clamps was lifted and I knew she had tied them to one of the hooks in the ceiling so they were pulled taunt.

I heard the door open and then close again and I then bare feet on the floor. One of my cock mates had joined us. I could smell his scent as he moved closer to my face. Then the head of his cock touched my tongue. My mouth was held open so wide that it never touched my lips. I flicked my tongue against it and it flinched but it never stopped its forward motion. His balls touched my nose as he forced his way into my throat. I could only take a breath and swallow it. I fought against my gag reflex as his pubic mound pressed against my face.

Now a new sensation grabbed my attention - pressure at my anus, something forcing its way inside. It felt like a large dildo, large and long. 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 you have your mouth 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 as they 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 to be 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 suppose to enjoy this but I couldn't help but feel pleasure 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. Finally I was able to swallow for the first time in a while and I took it all. I could feel a string of cum across my lips and chin and I wished I could reach it to lick it off.

Fiona slowed her pace as well and let the long phallice pop out of my sore ass. I could still feel the amazing 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 guys worst nightmare to have an itch there that you cannot scratch. Just as I was thinking that 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. At the same time, I felt someone standing between my spread legs and a warm hard cock was pressed into my waiting 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 watching me take a real cock in my ass. I could also tell, that it was the largest of my friends because it was really stretching my sore anus. 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 crawl 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 and I could feel the clamps tightening on my nipples. Jolts of mixed pain and pleasure rippled through me from every point of contact.

"How does it feel to get fucked, my naught pet? Think you will be able to follow the rules after this?" Fiona crooned into my ear.

Shortly after that, yet another sensation startled me as she wrapped her hand around my straining member. It was sooo 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 it slid 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 started working my growing member in her hand to help it along. I wasn't fully hard for more than a minute before I felt another orgasm building but the cock in my mouth beat me to it. Being caught off guard, I struggled to swallow and ended up losing a large part of it across my nose and face. He even smeared the last few drops across my forehead as he stepped away. Normally I would suckle the last few drops while I cleaned his 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.

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

"Son of a bitch!" I yelled again squirming but not able to get away.

She didn't stop but the guy pounding my ass did. He pulled out quickly and circled around to my face where he sprayed stream after stream of jizz into my mouth and onto my face. As he subsided, he stuck his softening cock into my mouth.

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