That night, I let Tan fuck my ass. There was no point in protecting it anymore. My blackmailer had used it once and I assumed he'd use it again. It had been more enjoyable than I'd thought possible, and even if Tan was larger, I believed if he was gentle, it wouldn't be terrible.
As he made love to me that evening after I'd had my first orgasm, I asked him if he would like to put his cock in my ass. He stopped in surprise.
"I'd love to," Tan replied. "But it should be properly prepared for anal sex by stretching it out. I can get some plugs if you want to try it."
I lied. "After you told me you'd enjoy anal sex with me, I investigated the practice and got some plugs. I've been wearing them during the day to prepare."
"You're kidding!" He pulled out of my pussy.
"No, Tan. Not kidding. Here's the picture Suki took of the final pose we agreed on. You can see the plug in my butt."
I pulled my phone off the nightstand and showed him the picture. He whistled. "You're gorgeous, Brenda. This is wonderful. I can't believe you have a plug in your ass."
"Suki and Erin were surprised too, but they both like anal sex, so not as surprised as you are."
"They're lesbians. What do they know about anal sex?"
"Strap-ons apparently have more than one purpose."
"I suppose they do," he mused.
"Anyway, it's my first time," I lied again, "so you need to be very gentle and go slow. There's some lubricant in the nightstand." Actually, he needed to go slow as I didn't know if my anus would still be feeling the affects of yesterday's rape.
"I'll be gentle," he agreed. "You'll hardly know I'm in there."
"I doubt that's true, Mr. Tan; but I appreciate you taking your time."
He got the lube and carefully greased my butt and his cock. I was a little worried. The last plug had been as thick as Tan, at least around the widest point, but not as long. My blackmailer wasn't as big or long, so even though I'd cum for him, I was concerned Tan might hurt more.
When he'd thoroughly oiled us both, including using a finger to stretch me out a little, Tan put the head of his cock at my back door and pushed. Reluctantly, my ass parted for him, with a sharp twinge of pain. I flinched and he stopped.
"Does it hurt?" Tan asked.
"A little, but don't stop. Keep going until you're all the way in, then pause while I get used to your size."
He pushed harder and his head popped through. I sighed when it did as it was the widest part. He held still.
"You're so tight," he said.
"You're so big," I replied.
After a couple minutes, I said, "Very slowly, work yourself in deeper. I'll stop you if it's too much."
Without speaking, he nudged his way forward. It was uncomfortable, like the largest plug had been, but not intolerable. I was grunting a little, in a very unladylike manner, but getting by. Finally it stopped.
"I'm all the way in," Tan said, and I realized I could feel his ball sack dangling against my pussy and his short pubes tickling my bottom.
"Stop there," I instructed. "I'm still getting used to how deep you are."
Tan held still for me. I could feel his cock throbbing in my rectum, his pumping blood causing it to twitch slightly. I was so full. The largest plug and blackmailer's cock failing to fully prepare me for how full I was. Gradually, my rectum quit trying to squeeze him out and gradually relaxed more around his cock.
"Very slowly; you may move," I said.
Tan withdrew an inch or two, then inched forward. When I accepted that, he withdrew more, and pushed back in. Slowly and relentlessly, he started using his whole erection to fuck my ass, and I accommodated it. The discomfort of his movement eased and I felt the first twinges of pleasure building up in my pussy, as if my ass and pussy were connected somehow. Tan reached down and began playing with my clit, intensifying my mounting pleasure.
"Do you like my ass?" I moaned to him. "Do you like fucking my ass?"
"Do I," he grunted back to me. "You're so fucking tight; it's like you're strangling my cock."
He sped up more, and I tolerated it, even reveled in it. He was fucking my ass almost as hard as he usually pounded my pussy and I was loving it. He pinched a nipple while he fucked me, continuing to tease my clit as well.
I screamed for him, "I'm cumming, Tan. You're fucking my ass and I'm cumming."
My whole body convulsed, bearing down on his cock. I felt him him expand in my butt and his cock pulsed, shooting jet after jet of his cum deep inside my bowels. We were both shaking, almost as if we were cold, as our orgasms swept through us like a rip tide. The sensations eased and Tan pulled me down, collapsing on our sides, breathing hard. His cock was still in me, but I felt it start to dwindle in size.
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