It seemed like nothing happened for a very long time though it was probably less than a minute. I noticed my breathing and tried to relax. I trusted her completely, but she always seemed to have another surprise for me. I flinched as something cold and wet touched my anus. It was very precise, only touching the tiny puckered hole. I must have been spread so wide that the gap between my cheeks gave her easy access.
She tapped against my hole making me realize what she was waiting for. I let out the breath I hadn't realized I was holding and unclenched. Immediately, I felt her finger slip easily into me with the dollop of cool gel lubricant. She pushed slowly but firmly until I could feel her other fingers pressed against me. She used a twisting motion to spread the lubricant around and pierce the inner sphincter as well. She withdrew, and in a moment I felt another touch, something larger and harder and colder. She pressed and I tried to relax and accept what felt like an ostrich egg into my tight hole. I'm sure it wasn't really that large, but it was definitely larger than anything she had used before. I took short breaths and then exhaled as she worked it in slowly, letting me stretch a little at a time to accommodate the ever increasing girth. She always told me that she wanted me to learn to love and even crave having something in my ass so she never wanted to hurt me or make the experience bad, but she was intended to train me to take larger plugs and, eventually she expected me to wear a plug almost all the time. The thought of being out in public or hanging out with friends while secretly having a plug in my ass seemed like something I could never bring myself to do.
This plug seemed like it was never going to end, but once its largest circumference had finally passed the outer and inner bands, my ass seemed to draw it in the rest of the way of its own accord At long last, my little outer ring nestled into the narrow (less thick) band just above the base.. It was still keeping me stretched and the muscle ring kept trying to close against the intruder, but after a few more short breaths in and out, it was not more than I could stand, and the large bulb was now wedged deep inside making me feel very full.
That's when I felt it start to humm. It was not the typical vibrator buzz, but more of a throbbing I could feel in my core and right against my prostate. It was just fast enough to feel really good but slow enough to be just a tease. Just as I started to get into its rhythm, it changed. It seemed to be on some random setting that would change speed, pattern and intensity every so often, never quite letting me get used to it. I would catch my breath when one of the more intense vibrations kicked in, and I couldn't help but sigh when it switched to a more pleasurable sensation.
I was left alone again for I don't know how long as I was lost inside my own ass. I must have been squirming (which she hates) from the feelings inside me because I was shocked back to reality by a hard smack on the head of my cock. She had told me on many occasions that I was not allowed to squirm, but she had never done that before. The sting momentarily softened my erection slightly, but I settled down. The harsh awakening had also left me feeling how stretched and full I was. I longed to move it just a little, something, anything, to ease the pressure. I pushed a little but it didn't budge, I tried squeezing it in but I was already at my limit. There was only the irregular throb in my ass, the strong beat in my ears, the gag filling my mouth, the total enveloping darkness, and after a few more minutes I was starting to slip back into the zone.
The next startling sensation was on my chest. She traced a circle around each of my nipples with something hard and pointed. With everything else going on, the touch made my whole body shiver. After a couple of minutes of teasing, the feeling changed to something very cold and wet - she was using an ice cube to circle closer and closer to my ever hardening nipple. I should have expected what came next but in my current condition the bite of the clamp was a complete surprise that would have made me cry out except for the gag in my mouth. She had only used the clamps on me once before. My nipples were so small it had been hard for her to get them on last time. Now, with the ice and my current state of arousal, she didn't seem to have any trouble. She repeated the process on the other side, the clamp was still a bit of a shock when it latched onto my nipple even though I knew it was coming this time. Once she had them firmly attached, there was a slight tug on both sides as she tied the center of the chain too the steel ring above the table and pulled it just taut enough that even the slightest movement from me could be felt through my nipples like an electric current.
More long minutes ticked by, my anus and nipples both aching with both pleasure and pain, but the anticipation of what might be next was worse...then it came. A hard swipe from one of her floggers right across my left inner thigh. Then another on the right. She got into a rhythm as she continued. I was desperately trying not to move but each blow made me flinch sending a shock into my nipples. She moved to my buttocks, making me clench against the thick plug. Then up to my stomach and then, unbelievably, to my cock and balls. She was a bit more gentle there, but the sensation was so relentless that it brought tears to my eyes behind the mask and I twisted pointlessly trying to avoid the blows, screaming silently..
When she finally stopped, I could feel the heat radiating from where she had flogged me. The stinging sensations lingered. My hardness had withered under the assault but now I felt her grip my cock in her hand. She was kneading it with some kind of lotion that was providing some relief. My erection began to grow again as she continued to tug and stroke it back to life. When I was fully hard again (possibly harder than I had ever been in my life) she stopped.
It seemed to be a much longer interval before I felt her touch again. She was up at the top of the chair. She reached behind my head and undid the clasp for the penis gag, then pulled it out of my mouth. It felt good to relax my jaw. She pressed her finger to my lips again to remind me not to speak, then she helped me raise my head slightly so she could remove the headrest from the chair. This allowed my head to hang over the edge so my face was upside down. I felt her move in closer and then she pressed her lips against mine for a long deep kiss. She stroked my cheek as she pulled away.
Another long pause let my anticipation build even more. The plug in my ass shifted its pattern again, drawing my attention. My nipples ached. The music still blocked out all other sounds. Ages seemed to pass before I felt her presence at the top of the chair again. Something touched my lips and I opened my mouth, assuming it was another gag. As it entered my mouth, I could tell it was something different, and there was a smell I didn't recognize. The thing was warm and hard but fleshy. In my sexual stupor didn't fully realize what it was until it was pushed deeper and I felt something swing forward and bump against my nose. It was another man's cock! I started to say "No", but it just pushed farther into my mouth and I felt Fiona's hand under my chin, pressing to close my lips around it. I struggled to spit it out but his legs were now on either side of my head and there was no way I could move that would give me space to remove it. He pushed forward again and I felt it twinge and start to grow larger and more firm. I felt a hard smack on my already sore ass cheek. Not the flogger this time, maybe a paddle. After several hard licks, the intensity of the throbbing in my ass was increased and I moaned. She was trying both the carrot and the stick. The dick in my mouth grew even harder and I tasted pre-cum that was not my own. She gave me a half dozen more hard smacks on my ass and then she grabbed my balls in her hand. I quickly realized that I was in no position to win this battle. I vocalized my concession as best I could around the cock that was now filling my mouth, and then I started to suck.
Fiona released my balls a moment later and patted my stomach to signal her approval. Surprisingly, my own cock never seemed to lose any of its strength through this ordeal. It just tingled and felt harder than ever. Now that I seemed to be more willing, the unknown man started to slowly pump his cock in and out of my mouth. The head of his cock felt like it had doubled in size and pulled out until my lips were locked in the narrow ring just below the head, then plunged back in, going deeper and deeper until I could feel him touching the back of my throat. I gagged the first few times but he didn't stop pumping, only pulled back a little to let me catch my breath and swallow. We finally got into a good rhythm that wasn't making me gag while I was taking the majority of his shaft on each stroke. I could sense that Fiona was guiding him so that, like like with anal, she could teach me to enjoy this.
Fiona must have just been standing back enjoying the show for a while because I couldn't feel her presence. I thought about what I enjoyed when I received a blowjob from Fiona and I tried to mimic that hoping to speed up this process and get it over with. I started using my tongue to tease him as he pulled out. He seemed to like this so much, he started pausing when only the head remained so I could swirl my tongue around it and use the tip to probe the slit at the end. After a couple of moments of that, he would push back into me feeling bigger and harder than ever, his heavy balls slapping against the bridge of my nose. My attention was being drawn to so many places now - my nipples were begging to be released, my poor little anus seemed to have finally accepted the huge droning plug but its affect on my prostate was starting to make me drool semen, and this huge cock fucking my face.