I had been saying no for weeks, his finger tentatively grazing over my asshole when we fucked, and me, stubbornly refusing. But every time he removed his finger, a sly smile would wash over his face and a groan. He respected my limits, however much he knew I would like it and I knew I would eventually say yes. Despite this he had the playful look of a child caught in the act, frustrated at being unable to play with a new toy - it’s a look that made me desire him every time.
I just couldn’t shake the negativity, the unfamiliar sensation and that part of the brain that knows what generally happens in that region. But from the very beginning of my Kinky journey I vowed that I would explore, try and then make an informed decision. I wanted to test my limits, in what my brain and body could endure and enjoy, trying to break my preconceived ideas of what I liked.
So, with the Sailors encouragement, we talked a lot about it. How it would feel, our erotic fantasies, and he helped put me at ease. First a finger, then a glass butt plug, then a ribbed glass dildo, then his cock. It started to feel...interesting...almost good. Uncomfortable but a pleasurable form of discomfort. We talked about it, I said it wasn’t the main event and that it added to sex but I thought I would never be able to cum just from that sensation. He vowed to prove me wrong.
In the end it took a play session involving rope and restraint, vulnerable to the whims of the Sailor, for my brain and body to unite. My mind and body was prepared, I had thought about it for a while, finding in the days leading up to seeing him, when I was horny, my ass muscles would clench instead of my pussy. It was confusing but I decided to see where it would take me.
The Sailor had great plans to play with me that evening while I was tied in his rope to the bed. Exploring my pain threshold with candles, ice and a flogger. Pleasuring me with his mouth and tongue and vibrators, making me cum again and again. Finally fucking me with my butt plug in, the bed clothes soaked from my squirting.
And it was in that moment, I wanted it. I wanted him to fuck my ass. We had done it before, but it was different this time. I actually wanted to feel him there, I was the one asking. So the Sailor, smile as broad as anything, happily, almost gleefully obliged. He had known all along I would get there and this was the moment.
He removed the plug still in my ass and began to suck on my sensitive nipples, making me moan and writhe on the bed. Meanwhile he made himself hard again with his hand, jacking himself off, while using his knuckles to rub up and down my pussy. It was our tried and tested technique and we both knew the result for me...an orgasm that often made me see stars and my pussy gushing all over him again and again as the waves hit me. It was intense, but not as intense as what was to come.
The Sailor used my own lubrication to coat his cock before aiming at his target. Slowly, ever so slowly, he inched in and out. To my delight, my ass muscles accommodated him easily and the sweet sensation of slow movement sent hungry signals to my brain. I wanted more. I wanted all of him. I wanted him to fuck me. So I clung onto his chest and growled in his ear, “Harder Sailor!” As ordered, he sped up, his whole length shooting incredible pleasure into my body. The warm, solid length of the Sailor fucking me was delicious and, before I knew what was happening, the most intense orgasm ripped through me as I squirted all over us.
I wanted to continue but it began to hurt and I told him to slow down, almost to a stop but still inside me. However, as he slowed down, the sensation became pleasurable again, and I eventually growled at him to fuck me again. We continued in this manner until I could not take any more, finally giving him permission to spray his warm cum in my ass.
Butt plug inserted to keep his cum inside me, he grinned at me, “I knew you would enjoy it”.
I remained silent. I would not give him the satisfaction to know he was right. I wouldn’t dare tell him I couldn’t believe how pleasurable it had been. That I now craved his cock, that my ass hole quivers at the thought of it. That, although I knew I was a squirter, I couldn’t really believe how wet the bed. That, if I were to become his butt slut, we would need more towels.
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