"Oh my God, that hurts" I screamed as Heather drove the bright red jelly dildo deep into my ass. She thrust with all she had, until the base of the dildo, probably 11 inches to the balls, was firmly planted deep in my searing asshole.
I was on my knees and elbows, face planted in the mattress with my ass in the air to give her easier access. She was behind me on her knees.
We had played many games where she had gotten fucked by numerous men, many times they were strangers, had her pussy stretched, her nipples tortured, or just generally treated like a slut, but I had had my share too. I had watched her fuck a lot of men, I had been tied up while a dominatrix flogged me and then I had to lie on a bed and hold the dildo against Heather's pussy while she fucked the dominatrix and her slave, a male, sucked my cock. I had been tied up, blindfolded, had my nipples tortured, my balls tortured, and even been pissed on.
But tonight, she had ideas of her own. She was going to fuck ME. She was going to fuck me in the ass with the same huge dildo I used to stretch her pussy out. She was going to tie me up and spend as long as she had to in order to make it fit in my asshole.
She started out licking my ass, a new sensation for sure, while stroking my erect cock with her hands. I was definitely hard and into it, because I was up for anything out of the ordinary.
The more she stroked my cock, the more enthusiastically she sucked and licked my ass, finally concentrating a little more on my asshole itself.
Then, she stopped stroking my cock and began circling my asshole with her fingers. She rubbed gently with a fingertip ad I could feel her long nails scraping just a little. She wasn't pressing hard enough to hurt, but it felt like she could have hurt me if she had wanted.
Then, she began to subtly put pressure on my anus with her fingertips, letting the fleshy part of her fingertips drag across my puckering hole as she let saliva drip from her lips.
She explored my ass just enough to let me relax a little before she began to stick the tip of her finger in my waiting ass.
"MMM" I moaned as her first thin finger entered the edge of my ass.
"You like it, don't you, bitch?" she asked.
"Yes" I replied in a whisper.
"Tell me deeper" she said forcefully.
"Deeper" I begged. "Please."
She began to fuck me a little with her tiny finger. She was thin and had long, delicate, thin fingers and it was no problem to get one in, but I knew more were coming.
Her finger fucked my about an inch, then a little more, and a little more, until she was fucking my ass with the entire length of one delicate finger.
Then, she surprised me. Rather than insert the middle finger next to the index finger she had buried in my ass, she began to try to work her other index finger in.
"MMMM" I groaned. This was still not much of a challenge, but I was beginning to notice. "Go ahead."
She spit on my ass and began to work the other finger in. She began to fuck me with her two index fingers, alternating thrusts in my ass. The feeling of pressure was intense, but it didn't hurt. It did seem, however, like she was trying to make it hurt.
That was fine with me. We had played games that had involved pain before, and as long as it didn't involve blood, I was fine. I liked intense, and I sometimes pushed my own pain boundaries when I was alone.
She fucked my harder and deeper with two fingers, and then began to work inserting one more from each hand. Finally, she had four fingers from each hand in my asshole and alternately fucked me with them.
"How does it fee. Bitch?" she asked fucking harder and harder. The more she pushed me, or the more it seemed to hurt, the more she seemed to be getting off on it.
I was happy with that. That was the way I wanted it.
She stopped, and reached for a box of latex gloves with a smile on her face.
"Now, I am going to fist that ass!"
I didn't know what to say. I wanted to encourage her, and that seemed to be accomplished best by acting fearful, but I was certain that there would be no problem getting her tiny fist in my already stretched ass. So, I faked it, hoping that being excited would cause her to push further.
"No" I said. "I can't take that yet."
She pushed her gloved finger easily into may ass and started fucking easily up to her palms. Then, she inserted her thumb and pushed.
It went in, but not as easily as I had thought it would.
"AAA" I moaned in pain as she managed to get her whole fist in.
"MMMM" she said. "That's what I want to hear."
She fucked me for several minutes with her balled up fist, finally working it in and out. Every time her fist crossed the threshold of my ass, I groaned, and I wasn't faking it.
It hurt, but it was good pain. It was pain that I was enjoying, and it seemed she was as well. And soon, she had my ass stretched enough that even her fist was not hurting.
