With a hand still on my ass, I felt Juliet start to explore my body. She used a couple fingers to tease the outside of my pussy lips, and her thumb massaged around my asshole.
"I think," Juliet said, "that what would please your mistress the most would be to fuck that little asshole of yours." And she pressed harder with her thumb into my hole. "You have done this before, haven't you."
My eyes went wide. I had experimented with butt stuff before, but it never gone much further than a finger. But I was eager to please her so I nodded.
"Good," Juliet said huskily. "First let's get you nice and wet." I felt her kneel down behind me, and I felt her wet tongue suddenly assaulting my asshole. It felt much different than getting my pussy licked, much less directly stimulating, but I loved it still. She spit right on my asshole, and then on my cheek. I moaned at the thought of something so dirty being done to me. She even stuck her tongue as far into the asshole as it would go.
Finally, she was satisfied that I was sufficiently wet and back up away from me. It was time. I was scared. I was ready.
Juliet tentatively pressed the head of the dildo against my opening. I felt the contours of the penis-like head. I knew it was going to be tight, and it might even hurt, but I was determined to please her. "Such a pretty little asshole," Juliet commented.
"It's yours mistress. Please take me."
"Good girl." And she pushed the head of the strapon inside of me. Immediately, I could feel it stretching my walls. It was definitely big. It even hurt a little bit, causing me to gasp.
Juliet must have heard, because she slowed down after I did so. She was a caring mistress, and only continued after a few minutes, when the pain subsided. "I'm okay, mistress," I assured her. "You can fuck me however you'd like."
Encouraged by this, she slapped my ass and pushed deeper. She was deeper inside of my than anything had been before. The pain was over now, and I was starting to enjoy it. After waiting a few more moments, Juliet started to thrust. In and out. Slowly. Making sure I felt every inch. And boy did I feel it.
"Ohhh, Mistress," I moaned.
"You like that, slut?"
"Yes mistress! It feels, ohhh, so good."
Finally satisfied that I was comfortable, it was time for Juliet to kick things up a knotch.
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