Ryan and I mostly played with ropes. He seemed content with vanilla, penis-in-vagina sex, just framed in ropes. I probably wasn't his most flexible subject, but I did start taking yoga classes at his behest, and I did let him take photos and share the ones that didn't show my face. Over time, we became what could be characterized as friends with benefits. We'd developed a level of trust in each other that allowed us both to push our boundaries.
Our relationship got to the point that I could help him fulfill the fantasy of having his trans housemaid around, cleaning and doing chores, while Ryan tied me up and fucked me (which, incidentally, fulfilled the housemaid's fantasy of being used only for housekeeping and being humiliated that she wasn't used for sex while, at the same time, being able to watch us). And Ryan was the one who coaxed me into anal sex for the first time. In a way, this little story is Mr Myrrh's way of thanking him for my fearless excitement and love for anal.
I don't recall my ex ever expressing an interest in it. His fingers never strayed near anything down there when we had sex and he was quick to apologize if his penis missed my pussy and slid toward my bottom; he tended to lavish his love on my breasts and nipples, which I appreciated. But, still, I thought about anal. I secretly read about it and looked at pictures and wondered if it really was as painful as others said. When we separated and I started on my thrilling little adventures, anal play and anal sex occasionally came up and I always said no; I was too afraid.
The day I said yes, I was on a mat on the floor. Ryan was looping rope around my ankles and I was already starting to fall into that very relaxed state of being, letting myself be "done to." We were talking, but I don't remember what we were discussing, when he changed the subject and asked me to confirm that I'd never had a cock up my ass. That's exactly how he asked the question: no introduction, use of completely crass words. That's how he always asked questions. I was usually surprised enough to answer honestly.
"No, I haven't. But I want to. I think," I said, trying not to blush. Funny how a person can feel embarrassed by words. He had already fingered my ass a few times during previous playtimes, pushing his way in with a thumb or finger, usually when I was about to come, the sensation pushing me over the edge.
"You think?" he parroted, grinning. But he wasn't looking at me, he appeared to be focusing on the ropes, tying a knot.
"I mean. I'd really like to, but I don't want it to hurt. Maybe I need anal training first," I said, trying out an idea I'd heard before.
"Maybe," he nodded. He shifted himself up closer to my torso and pushed me around to get the rope where he wanted it to go, around my waist. I liked being pushed around physically like that, gentle but purposeful, reminiscent of letting the ocean push me around as I floated on my back, sort of scared but still trusting some huge force that could crush me at will.
"Maybe," he repeated, then changed the subject to the possibility of installing a second eye bolt in the ceiling so he could get more creative about multiple-point suspensions. The rest of our playtime was spent finishing up the rope work then playing with the Hitachi, clothespins, and my favorite flogger. I was bent over a padded bench set on a raised box of wood, nearly every bit of me accessible to Ryan without him having to bend or kneel or squat. After my second orgasm, when I was feeling completely open and liquid, I felt his fingers at the entrance to my bottom. I was too tired to worry, much less seize up.
"Would you like me to help you with anal training now?" Ryan asked.
"Mmmm," I managed.
"Come again?" he said in his teasing voice.
"Yes, please, I would," I said.
"A complete sentence, please," he said, sounding more demanding.
I vaguely wanted to throw something at him but, instead I said, "Please help me with anal training," in my most contrite and submissive voice.
"You're a good girl," he said gently as he pushed a lubed finger into my ass. I felt myself melt a little more, both at his words and at the feeling of the intrusion.
He slid his finger all the way out, circled the tip of it lightly around the entrance, then slid it all the way in again. I groaned when he withdrew it once again.
"Please," I managed, "Please. More?"
"Point one," he said, ignoring my plea, "When you feel me press against your asshole, think and imagine your hole opening to me. Your brain controls the dilation of that muscle. It does it automatically when you have a bowel movement, but you can consciously control it. Practice that now." And he pushed what felt like the flat of his fingertip against me. I thought, "open," and imagined the kind of anal gape I've seen in pictures. I could feel my muscles begin to relax and open, yielding to the gentle press of his finger.
"Very good," he said, in that slow, sweet, sexy way of his. He began to fuck my ass with his finger, moving it slowly in and out of me. I moaned and pushed my bottom toward him as much as I could within the constraints of the rope.
"Point two," he said, continuing to finger-fuck me, "The more lube we use, the easier it is for your muscles to relax. If you're finding it difficult to relax, let me know and I'll apply more lubricant. Okay?"
"Okay," I managed to gasp. It was proving difficult to focus on his words. He fucked me with his finger for another moment before withdrawing again. I wanted it back in so badly. Then, I felt a second, cooler finger join the first at the entrance to my hole. I thought, "open," again and was surprised and excited to discover that two fingers seemed to slip in as easily as just one.
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To be continued tomorrow.
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