“So have you ever played with a real sex toy?” he asked. I shook my head. “No master.”
“I thought so. I’ll make it easier on you.” He said and grabbed something from his pocket. It was a tiny black bottle with a naked man on it. He uncapped it and poured some of the slick liquid over the rubber toy. It shone all over now and looked inviting. I turned myself and stared at the breakfast table while I lowered myself to the toy.
I grabbed the edges of the chair so I could carry my weight as I moved my hips back and forward, aligning my hole with the tip of the toy. Once I had found it I slowly lowered myself.
I opened up. Slowly my hole accepted the toy as I went further down. The first inch was fine, but nearing the seconds the toy got wider and I felt the pressure increase. At the third inch it started to really hurt and nearing the last inch, at the widest part of the toy I couldn’t take it anymore. I held my weight but stopped moving.
“I’m sorry, I’m sorry I can’t.” I breathed. Gerard moved slowly and placed both his hands on my hips. He didn’t push me down but kept me from going back up.
As gentle as a lover he whispered “I’m sorry, what?”.
I started to sweat all over and felt my face burning. “I’m sorry master.” I quickly said.
Gerard let go and I moved myself back up, away from the pain and pressure. The moment the toy exited my toy a rush of pure pleasure washed over me. I let out a high pitched girly moan that embarrassed me to no end. Gerard chuckled.
“You know, it’s called a toy for a reason. Don’t force yourself on there, play with it.” He told me patiently.
I was glad he didn’t say anything about the sound I had made. Shivering I lowered myself to the toy again. It would never work, I thought.
The first inch went in easy again. But Gerard stopped me when I went lower. He placed both his hands on either cheek, carrying my weight.
“You need to ride it a little” he told me and lifted me a tiny bit, then lowered me. Again I made that weird childish moan. I bit my lip and Gerard removed his hands. I quickly carried my own weight before I slipped down.
He caressed his thumb over my lip. “No no no Lex. Don’t be ashamed. Let yourself go.”
I opened my mouth and let out a long satisfying ‘ah’. Gerard smiled and cupped my face.
I couldn’t think anymore. I was so aroused. I knew he was enjoying my hard cock and my embarrassed face but I couldn’t stop myself.
“Ride it” he whispered.
I obeyed. I moved my butt up and down. It felt amazing. At first it was just the rubber sliding along my opening. But I started to realize I was holding the chair. Both my arms were nowhere near my ass that was being filled. My own body started to move faster. The room filled itself with my moans and all I wanted was more. More and deeper.
The intense pressure started to feel good and dirty. There was an actual toy in me.
It went deeper and deeper. My cock was twitching and throbbing. I let myself go and with one final thrust I lowered my body over the last inch. There was a tiny hint of pain but then my hole closed itself over the final smaller part of the toy. I was plugged.
My own butt was stuck to this chair, plugged and caught by a real toy. I was breathing loudly and my nails hurt from digging themselves into the chair.
Gerard softly massaged my belly and chest and I leaned back. It was over. The toy felt a bit annoying so I spread my legs as far as I could, easing the pressure.
I couldn’t help myself and grabbed my balls and pulled them up. It was a strange sight. I could see the toy just disappear in my own body. I smiled proudly to Gerard.
“Perfect.” He told me and moved behind me.
He slid the chair towards the table and I yelled out loudly. The scratching of the chair over the floor sent vibrations all throughout my body. I leaned forward and grabbed my tummy with both my arms where the vibrations had been. Breathing loudly again.
Gerard grabbed my shoulders and gave me a very intense and relaxing massage.
“Just relax yourself, you’ll get used to it.” He comforted me.
Once my breathing had slowed and I could open my eyes again he stopped and settled himself on his own chair.
“And?” he asked while he grabbed some bread “How does it feel?” he asked me.
I shrugged as much as I dared. It felt as if any movement I made would stop the pleasure and start pain. “I… I don’t know, master” I stammered.
“Well does it hurt?” he asked.
I shook my head slowly. “No, master. It just feels… full” I said.
He chuckled again.
“Well I’m glad it didn’t hurt. It is the smallest buttplug I could find.” By the way he said it I knew what I had to say. I didn’t want to, but I felt so vulnerable I had to.
“Thank you, master” I softly whispered.
We started eating breakfast. It was difficult at first. Whenever I grabbed something from the table and moved back I whimpered and moaned. The toy didn’t hurt but my body kept telling me it was there. In my own ass. I felt dirty and vulnerable. My cock slowly went flaccid.
Gerard started chatting. About what my family had planned for the day. The great weather. How his night was.
I started to relax more. I started to enjoy myself. Then Gerard asked me how I figured out I am gay. The question took me by surprise. But suddenly I felt so relieved and happy. Throughout all this mess of him using me I had forgotten an important part. I now personally knew someone who knows about my sexuality. For the first time in my life I could openly talk about it.
I first answered him shortly, but quickly I opened up a waterfall of stories and feelings. How guilty I had felt. My first crush. The gay porn I watched. Everything.
Gerard listened with great care and patience.
Once I was done we were quiet for a bit. Then I asked him a question.
“How did you figure it out? Master.” I softly asked.
Gerard chuckled.
“That would be a complex story. And too personal. But how about I’ll tell you how I started training boys like you?” he offered in return.
I nodded.
“It comes with a small price though.” He said with a friendly smile and handed me a glass teacup.
“Fill it up. Just your precum though, no orgasms yet.” He ordered, then he grinned. “Oh and no hands either.”
I could have known. I actually kind of enjoyed the idea. I clasped the cup between my legs and lay my flaccid cock in the glass. My cock already made an imprint on the side with precum.
I shook my hips back and forward. Very slowly. It felt amazing and my cock increased in length with every thrust. Once it was pressing hard against the glass I stopped. I waited for it to go soft again and looked up at Gerard waiting for his story.
He started telling me how he first just watched boys and men jerk themselves on cam. How he thought it would arouse him but ended up just boring him. Until he met a boy online, “only half as cute as you though” he said with a smile, that wouldn’t mind giving him a little show.
He stopped talking here. My cock had gone soft and I was rocking back and forward with my body making it hard again. Once I had stopped and had my breath under control Gerard continued his story.