High School Glory Hole

By Beaumonte Bill / Oral Guy 2000

Published on Jul 18, 2020

Gay

High School Glory Hole (part 14)

A guy who is curious about sucking finds his curiosity satisfied when he encounters a glory hole — only to find that his life is forever changed! I hope you enjoy this work of fiction.

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That night as I climbed into bed between George's legs he said, "Tomorrow I start prepping you to be fucked."

I wasn't sure what prepping meant but was eager to find out! I sucked George off and held both his cock and load in my mouth as I drifted off to sleep. In the morning I awoke, and sucked George off once again. It just seemed so natural to have a cock in my mouth – I wondered what it would feel like up my ass.

George told me we would have to wait for Mom and Dad to leave, but once they did, we would start the prepping. In a few hours they were gone, and George said we had about four hours, which was more than enough time. He told me to get undressed and go into the bathroom. I waited naked in the bathroom for him.

George entered carrying a bulb-shaped object with a long thin nozzle a little less than an inch in diameter. "What's that?" I asked.

"It's Mom's douche syringe," he explained, "And she'd be really pissed about this, so keep this between us."

I promised to do so and watched with interest as George filled the bulb with warm water and screwed the nozzle back on. He had me kneel in the shower with my ass up in the air. He put lube on his fingers and pressed one into my hole, telling me to relax as he did. It felt kind of strange – something going into me there, but I knew it would be something special, so I just enjoyed the adventure. George worked his finger in and out and it began to feel really good. Then he removed his finger and pressed the douche nozzle in. It felt like a thick finger, and soon I felt the rush of warm water entering me as George squeezed the bulb. George squeezed a second time and more water entered me.

"Now I'm gonna remove it, so tighten up as I do so you don't leak all over," he said. It felt strange to have the warm water in me – it made me feel like I had to take a dump, but I squeezed tight as George withdrew the nozzle.

I felt a little water leak out and drip down my balls. "It's okay," said George, "That's why you're in the shower – now just hold it for a bit. I held the water in for a few minutes, and then George told me to sit on the toilet and expel. He left and told me to call him when I was done, and since I would stink the place up, use air freshener spray.

It felt good to expel the water, which took some of my bowel contents with it. I finished and wiped, needing more tissue than usual because it was messy. I sprayed and called out to George.

Upon his return he refilled the douche bulb. "Once may be enough," he said, "You'll learn from experience, but today we'll do more just to be sure."

I got back in the shower and put my ass up. Once again George pressed the nozzle into me – I was beginning to like this! After he filled me again, he had me wait, as before and the expel. We repeated it a third time, which George said was more than needed, but just wanted to be sure.

After wiping, spraying and calling George back, he told me to kneel in the shower once again. This time he didn't fill the bulb, but inserted the nozzle into me, pressing it in all the way, and then pulling it back, but not completely out. He repeated this over and over and I really got into it.

"This is what fucking is like," explained George, "Except cocks are a lot bigger, and I need to get you ready for that." He continued fucking me with the nozzle and then pulled out. I protested, but he assured me that more was yet to come.

"Now shower and make sure your ass is nice and clean," he ordered, "Soap up a finger and wash your hole good inside and out."

I showered and cleaned up thoroughly. I fingered my ass while stroking my cock – it was a really nice sensation I knew I was going to have quite a bit.

After drying off I went to see George, still naked. "Get dressed," George said, "We need to wait an hour before doing anything else."

"Why is that?" I asked.

"You expelled most of the water, but not all," he explained, "Your colon will absorb the rest over the next hour. If we do things too soon it can be messy – the dreaded "poop soup".

I wanted no part of that, so I got dressed and waited, wondering what would come next.

After an hour George had me get undressed and kneel on the bed. He lubed his fingers and pressed one into me which I received eagerly. Then he pressed a second one in, and spread them, stretching my hole. That was a strange feeling, but I welcomed it as part of my anal adventure. Then he inserted a third finger, and when he spread them it hurt just a bit and I cried out. George brought the fingers together and told me to just relax.

"I think you're ready now," he said. He showed me a dildo that was a little over an inch in diameter, and then proceeded to press it into me. It felt even better than his fingers and I was thrilled at the feeling as he stroked it in and out of me.

"I think you are ready for the next," he said, withdrawing the dildo. Next I felt something clearly larger pressing into me. I felt stretched wider than ever but it felt okay, and I cherished the feeling. Being larger, it gave me a more full feeling as he stroked in and out. He continued that for a few minutes and then pulled it out.

"Let's try the last one," he said, and pressed what must have been a huge dildo to my hole. As he pressed it in, I felt a blinding flash of pain and called out. George stopped and told me to just catch my breath and relax. I did, and then told him I was ready to try again. The head of the dildo opened me more than ever before and once again tremendous pain! I cried out and George stopped, but didn't pull it out.

"See if you can get used to that and tell me when you are ready to continue," George instructed, "It's almost in."

After a few minutes I told George to continue but once again the pain was too much, and George pulled the dildo out all the way.

I looked at it and immediately understood why it hurt. It was nearly a foot long and two inches across.

"I don't think I could ever take that!" I said.

"Sure you can," assured George, "With practice and lots of lube – but you gotta go slowly."

I rested and after a while I said, "I really want that in me, but is there a better way?"

George thought about it for a while and then said, "Get on your knees for a blowjob."

I did and George pressed the huge dildo between my cheeks, against my hole. He put the other end on the floor, and then stood in front of me, cock head pressed to my lips, which I eagerly opened to receive.

"Stroke as you suck, and when you are ready, press down on the dildo and see how far you can get," George directed.

I stroked as I sucked, enjoying the feeling of the dildo head pressed to my hole, and slowly pressed down on it. I stopped before it hurt and rose up again, but then pressed down. This was the most amazing experience for me. Stroking while sucking was wonderful, but the dildo took it to a new level. Each time I pressed down it seemed like I was going further, and finally the head was in all the way, and I sank down a few inches before "bottoming out".

As I rose up, the dildo slipped out, but I didn't let it come out all the way. I rode the monster dildo that way until George came, which soon sent me over the edge, and I came as well. George praised me and inspected me, seeing that the dildo was solidly inside me.

"You did well," he said, "And if you practice regularly you'll be ready for Dad's next poker party."

George told me that he would get me my own douche syringe, which I should keep hidden from Mom. I should practice using it and should clean myself out at least an hour before I get fucked.

"George," I asked, "Would you fuck me?"

"I'd love to," I said, "But Dad wants to give your virginity to one of his poker buddies. After that I'll be glad to do you."

From that point on, whenever we could I sucked George while riding the monster dildo, looking forward to a real cock in my ass.

–––––––––––––––––––– To be continued ...

Feel free to contact me with your comments or requests. –Bill (oral_guy_2000@yahoo.com)

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Next: Chapter 15


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