I leaned forward, opened my lips, and, for the first time in my life, felt a cock in my mouth. I was surprised by how wonderful it felt. My motions on her cock began tentatively but soon I was sucking her cock with ardor. I was no pro at this, as Kiera was. Compared to her, I was a rank amateur. (I remembered the origin of the word ‘amateur’–one who engages in an activity for the love of it. Appropriate now!)
Amateur or not, I was doing a good enough job to have a dramatic effect on Kiera’s cock. It swelled and hardened in my mouth. Its full length and girth wasn’t much–maybe five inches long and not much thicker than a jumbo hotdog. But, when I pulled my mouth off of it and beheld it, wet with my saliva, it confirmed my judgment that it was absolutely perfect.
I leaned forward to take her beautiful little cock back in my mouth, but Kiera had other ideas. She pushed me back onto the bed. She pulled up my legs by my knees and spread them.
Oh, shit! I thought. She wants to fuck me!
This was a whole ‘nother thing! It was a further, and scary, line to cross. Still, her finger had felt so good and the thought of her adorable little cock penetrating my ass held its attractions. In any case, I didn’t have long to dither about it. I felt the tip of her cock against my sphincter and, after she dribbled some more lube on it, I felt it press against my asshole.
“Look at me,” Kiera said as she increased the pressure on my sphincter, without actually entering me.
I had been looking at her, but not at her face. I’d been looking at the small, rigid dick as it approached its target. But now I looked up at Kiera. Our eyes locked as she looked down on me, flat on my back with my legs spread allowing her access to my bum. I saw her smile–not a smile of derision, but one of pleasure–as she ever so slowly pressed her cock into my ass.
Now I had another reason to appreciate the small size of Kiera’s cock. Not only was it aesthetically attractive–just perfect on her–it was also a very welcome feature given my inexperience with ass play. I’ve read enough Internet porn to be familiar with the “it hurt so good” trope. But I was relieved that the pleasure that Kiera’s cock was giving me hadn’t needed to be earned by a lot of pain along the way.
And, indeed, Kiera’s cock was giving me pleasure. There may have been no visible evidence of this, apart from the smile on my face. I wasn’t getting hard again. I’d just shot every bit of my load, after all. But I was learning that sexual pleasure wasn’t always about getting hard and stimulating your cock. I was finding a source, indeed a kind, of pleasure I hadn’t known before.
Without interrupting her rhythmic stimulation of my asshole, Kiera began playing with my utterly limp cock with one hand. That had the effect of emphasizing in my mind the fact that the pleasure I was feeling wasn’t from the stimulation of my cock.
Kiera could see the pleasure she was causing me with her cock and I could tell that her awareness of that intensified her pleasure, which in turn intensified mine.
“Push your hips up,” Kiera urged. “Let me get deep in your ass.”
I raised my hips, giving Kiera better access to my asshole and she pushed a pillow under me to keep me up at this angle.
Kiera got a good rhythm going and was thrusting as far into my ass as her diminutive cock allowed, she began urging me to beg for it. And, surprising myself, I did just that–and it wasn’t mere playacting.
“Come on, let me know how much you want it,” Kiera said. “Do you like my clitty in your boy pussy?”
“God, yes … fuck me! Fuck me harder.”
Kiera complied and soon she was spewing her spunk in my ass. Throughout this experience of losing my anal virginity, my own cock remained limp, flopping loosely whenever Kiera wasn’t fondling it. As a man–one who formerly, at least, thought of himself as straight–I’d always associated sexual pleasure with my cock. For me, sexual gratification had always meant my cock getting hard and shooting its load of cum. But Kiera had taught me something new. I could derive sexual satisfaction, a sort of climax without ejaculation, just from a cock fucking my ass.
When Kiera pulled her cock from my ass, there was a moment of awkwardness for me. What did my response to having Kiera take my anal virginity say about me? What would Kiera think about me?
Her nonchalant demeanor put me at ease, though. We both got dressed without saying much. Kiera said something like, “That wasn’t so bad, was it.” Not a question but a statement. She was right. In fact, it was so good that it worried me.
Matt and I hardly said anything on the way home. We each said our encounters were interesting and left it at that, both of us ruminating in our own memories. I felt a little moisture escaping from my ass. Clenching my ass muscle made my memories of Kiera fucking me even more vivid.
Tonight had been very different from what I’d expected. I’d crossed a line, to be sure. I didn’t really know what all lay in store for me on the other side of that line but I’d been so excited by my taste of it that I knew I’d be exploring it more.