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I hesitated. There was a part of me that still responded in fear at the prospect of anal. I had read it wasn’t supposed to hurt if done properly. But it had hurt when Kurt tried.
I couldn't help myself. "When I did it before, it felt like I had a knife inside of me."
He embraced me, kissing all over my face and then my mouth. "My poor sweet Katherine," he said, his voice a whisper. "I promise you when I do, you'll feel pleasure. Do you trust me to know how and when?"
I nodded, unable to speak.
For a moment, he was silent. He said nothing, he did nothing to me, but I felt his gaze on my face.
"It's just that I'm still so scared..."
"I know. That's why you have to trust me to know when you're ready."
I nodded and he kissed me once more. I relaxed a bit. Maybe tonight wasn't going to be the night. I knew he would eventually fuck me that way but not tonight. I sighed, exhaling heavily in relief.
He rose up and my body felt cold without him on top of me. Then I felt his fingers on my labia once more, stroking me, slipping inside of me. While he played with me with one hand, he licked and sucked my nipples once more and soon, despite my earlier anxiety and dread, I responded, my body aching, waiting for him to do what he would to make me come.
Once more I felt the cool wetness of lubricant on me and then something entered me, something cool and solid and thick – a dildo? It entered me only an inch or two, teasing the outside of my body while he continued to stroke my clit with his thumb. It felt so good to have something inside of me and something stimulating my clit. I groaned and wriggled under this attention.
He slid the dildo in a bit farther, stroking in and out slowly while rubbing my clit. Soon, the pleasure increased and I knew I could come. When it pressed at the right spot, I moaned.
"Master, I think…"
"Good girl," he said in reply, withdrawing the dildo, leaving me empty. Then, he pushed my knees up higher and his fingers stroked me, circling my anus, the tip of one slipping inside. He removed it and then I felt something cool press there. A butt plug. I tensed a bit.
"Relax, Katherine."
I tried, remembering what he
'd said the last time he used it. I took in a deep breath and tried to relax, blowing out the air and soon, the plug slipped inside of me, past my resistance. It felt larger than the one he used before.
Once more, I felt his thumb stroke my clit, and he slipped the dildo inside an inch or so. I tried to focus on the good sensations. In truth, the plug and dildo soon became one form of pressure and I focused on how good it all felt.
When I thought my orgasm would start, I tried to speak and he pulled back again, leaving me gasping. Then, he removed both toys and I felt immediately empty, the pleasant stretch of the two objects gone. He rose up and then he unclasped the cuffs on my ankles and wrists and turned me over so that I knelt on the edge of the bed with him behind me. His fingers were wet and slippery with lubricant and he once more teased my anus and slipped a finger inside. I tensed, inhaling deeply.
"Shh, Katherine," he whispered, his finger stopped inside me. When he tried to insert two fingers, I gasped.
"Master, I—" but he leaned down and kissed my shoulder, his fingers both now inside of me, slipping painlessly past my resistance, moving slowly in a circle as if trying to loosen me. We remained in that position for a moment, and soon I relaxed but in truth, my heart was beating faster. When he began teasing my clit with his thumb, the pleasure overcame the fear I had and I couldn't help but respond, my breathing increasing as well.
Finally, his fingers withdrew and the tip of his erection pressed there instead. I squeezed my eyes shut and bit my lip, waiting for the pain I remembered from before with Kurt. I felt my flesh widen, felt the slickness of the tip press inside, and it felt like intense pressure, but there was no pain. He bent over me a bit, one hand slipping under me to tease my clit while he continued to press his cock inside of me.
"Relax, Katherine," he said, his voice warm and soothing. I felt more cool wetness against me and he slipped his cock inside a bit more, meeting my resistance. "Exhale. Blow out your breath."
I did and then he was inside me a bit deeper. The pressure felt intense, and a burning began deep inside me, bordering on pain but nothing like when Kurt tried. I wanted so much to do this, for it to work, for me to like it. I tried to relax totally, to let my muscles slacken so he could enter me.
"It's too much…"
He pulled back a bit, the pressure lessening, the burning milder, but he didn't withdraw completely. More wetness, more pressure, but in truth, my lip hurt more from biting it than what he was doing to me.
"Drake, please, I don't want this. I don't know if I can do this," I said, gasping when the pressure grew even more intense.
"You already have," he replied, his voice thick with pleasure.
I frowned. "You're inside of me?"
"Yes," he said, his voice tight. "All of me."
We remained in that position for several long moments, him leaning over me, one hand holding himself up, the other hand around me and between my thighs, his fingers slowly stroking my clit, his cock filling me completely. He didn't move inside of me, but he remained in position. I didn't know if I could come like that, but soon, the pleasure grew strong enough to overcome the sensation of him stretching me so wide and I pressed against his fingers.
