A s I grew accustomed to Lou's huge cock inside me (see Part 11), I found that I really liked the "fullness" it gave me. I had a number of dildos, which I would often ride when I jacked-off, and sometimes during blowjobs. Some of the guys I blew really enjoyed watching me ride a dildo as I sucked them, often doing so in front of the full-length mirror in my hotel room.

Steven was one of them and took things to a whole new level. He told me that on his next visit he wanted to take charge of my ass, and said I should bring an assortment of dildos, including my largest one, and to stop by a grocery store and buy the biggest cucumber I could find. I also brought my digital camera, hoping to document the entire experience.

Anticipation for what was to come preoccupied my mind the entire day, and on my way back to my hotel room I stopped at a grocery store. I examined the cucumbers, wrapping my fingers around them to assess their girth. The one I bought was so thick that I could not touch my thumb to my fingers when wrapped around it – it was even thicker than Lou!

Arriving at my room, I took a quick enema so I would be nice and clean and have plenty of room for penetration. When Steven arrived, I greeted him at the door naked and he quickly entered. I had the dildos and cucumber laid out on a towel on the bed and he smiled as he examined them. He picked up the cucumber and asked, "You really think you can take this?"

"I don't know," I nervously replied.

"Don't worry, you will," Steven replied, "I'll make sure of it." I feared that I was in for some serious pain.

There was a large ottoman footstool in my room and Steven had me lay over it. Steven squirted a lot of lube between my cheeks and in my hole, and then slipped three fingers in. He didn't even start with one, but went to three immediately, spreading them to open me up. He took pictures of my ass in various stages of submission.

Soon the smaller dildo slipped in fairly quickly, going in right to the base. They were short, so it didn't "bottom-out". Steven took pictures as each entered me, as well as fully inserted. I was enjoying it so far, but he hadn't gotten to the big ones yet. Steven pressed the second-biggest dildo to my hole, and met some resistance, which didn't deter him in the least. He pressed into me, causing me a little pain, but very tolerable. I reasoned that if I was going to get it up the ass, I had to be willing to endure some pain. Steven pushed it in all the way, bottoming out. He tried to push it in further, but kept bottoming out, causing me discomfort.

"That's all I can take," I said.

"Too bad," Steven said, "I was hoping you could take it deep."

He pulled out the dildo and was now ready to insert the largest one. This one was bigger than Lou, and while I'd had it in me a couple of times, I had to work up to it slowly, and found it was just a little too big for comfort.

Now, in Steven's hands, that monster dildo was about to rape me. "Please go slow," I begged Steven, and in response he said he would, but I was going to take it, as well as the cucumber. That cucumber just might be more than I could take, and I began to regret agreeing to this arrangement. I felt the head of the biggest dildo spreading me open. It didn't go in easily, and Steven was working the head back and forth while pressing into me, and soon it entered me, hurting as it penetrated. Steven paused to take a couple more pictures and then pressed it in as far as it could go.

"Ready for the cucumber?" Steven asked after the dildo had been in me for about five minutes.

I said I was, and he removed the dildo. Now I felt the end of the cucumber slip into me. It went in easily because it was tapered, but soon I felt it stretching me as the thicker part slipped in. Meeting resistance, Steven continued to press, saying, "You're gonna take this, no matter what."

I pushed back, as if taking a dump, and the widest part slipped in. Steven tried to push it all the way in, but it wouldn't go any further. Steven took his final pictures, showing just the tip of the cucumber protruding from my completely filled ass!

"Now it's time for you to repay my kindness," Steven said, and ordered me onto my knees to blow him. I had to keep the cucumber in me until he left, and had to hold it in place with one hand while I sucked. Steven was already quite aroused from all that we'd done, and quickly came. He pulled out and I remained kneeling, holding his load in my mouth and the cucumber in my ass. When he zipped up and left, I went into the bathroom and removed the cucumber. I looked at it in disbelief, amazed that I could have had it in me!

I put it in a plastic bag for disposal down the hall (I never left evidence in my room waste basket). I cleaned up and sat on the bed, reviewing the pictures Steven had taken. As agreed, I emailed him the pictures and thanked him. By that time, I really had to cum, and jacked-off before turning in for the night.

My ass tingled for the next two days – a reminder that I wasn't like most other guys!

  To be continued . . .

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