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I never even thought about anal sex until I met Gary. He was really into it. I was disgusted at first at the idea, but he was very persuasive and since I loved him and wanted to please him, I agreed to try it.

You would never guess that Gary is the type of guy who would be into anal sex. Clean cut, blonde hair, ruddy complexion. He's very conservative, wears a suit and tie every day, works in middle management. But, in the bedroom, he's a maniac.

So. My first night trying anal. The first thing Gary said was, "let's get you clean." My eyes widened as he pulled out an enormous enema bag with a very long hose. He commanded me to get on all fours in the bathtub, and I complied. He filled the bag with what seemed like gallons of warm soapy water and said, "relax."

He slowly inserted the hose into my tight rosebud. Even *that* felt a little painful, but he stroked my hair and actually reached down and flicked my clit for a little bit, so I finally could open up and relax. He stuck a few fingers in my cunt and slowly but surely, I felt my rosebud open to his enema hose. He moved the hose around a little, in and out. I could feel my rose opening.

Then, he released the water into my anal cavity. Suddenly, my belly got bigger and bigger and bigger as the water filled me up. He pulled out the hose with a quick POP and then said, "hold it in".

I was on all fours for what seemed like forever. He kissed me and stroked my hair, and began massaging my nipples, which were huge and extended, my tits hanging down. It was hard to hold in the water, but I managed. Finally, he said "release" and I let all the water gush out.

I was surprised at how dirty the water was. But he cleaned me all up and made sure I was squeaky clean before proceeding. The first thing he did was show me a series of dildos, from small to large. He picked up the small one first. "Let's see how you do with this", he said. My eyes widened. Even though it was the smallest one, it still looked huge!

Gary got out the lube and began to lube up the dildo. He then put some on his fingers and began massaging my ass, letting the lube drip slowly onto my tight rosebud. His fingers lingered at the entrance and I felt my self instinctively tighten up as he teased the opening. "Relax," he commanded and flicked my clit to remind me of who is boss. He tweaked my nipples a bit and stuck a few fingers in my cunt. "Ride these fingers," he said and I began to buck against his powerful thick fingers, like a rocky horse. "That's it" he said. "Good girl."

After riding his fingers, I did feel more relaxed, and then Gary took the tip of the dildo and slowly began to insert it into my rosebud. I moaned and he worked it in, but slowly, slowly, so as not to hurt me. Suddenly, it was all in! He held it there.

"What do you think?" he said, grinning. I smiled back. "It's okay, I guess". "Good," he said, "let's try the next size." He pulled the small dildo out with a POP and I gasped. He laughed and pulled out the next-largest dildo and it was the same thing, except this time, it hurt going in and he had to go slower. "It hurts" I said and he stopped and put more lube on. Then, he tweaked my nipples, which were by now huge and as he tweaked them, he slowly pushed the dildo in a little further until it was all the way in!

I gasped. He took out his phone and photographed the second dildo in there. "You're really getting stretched out" he said. "But I know you can do better. I have to prepare you for my cock." He pulled the second dildo out with a POP!

He pulled out the third dildo, which was enormous. Much bigger than his cock, although not by much. "I don't think I can take that" I moaned, but he stuck a few fingers in my cunt and made me ride them while he tweaked my nipples and stuck the second dildo in my mouth to quiet me, and as I rocked back and forth riding his fingers, he started to work the largest dildo in my rosebud.

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