Chapter 4

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 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 pausing 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. Devilish nipple clamps came next, and her latest new toy was an anal hook with 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 my own ass could be, and also how hard it could keep my 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 most mornings 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 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 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 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 three of my friends knew I was now 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 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 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 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, 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 taut.

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. It was the long cock. 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 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 then my 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 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 guy’s 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. It was the regular-sized guy. At the same time, I felt someone standing between my spread legs and a warm hard cock was pressed into my waiting hole. 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?