The First Time (from Memory...this Was So Long Ago!)

I had often fantasized about anal intrusion during my masturbatory sessions. Anal sex seemed to be the final frontier of forced entry and domination which pervades so much of my personal fantasy world. Yet, I had never done it. A few clumsy and boorish attempts, made mostly by a poorly aimed and overeager phallis were instantly uncomfortable (read…it HURT)…so, I quickly pulled forward and guided the penis to the known comfort of my waiting *****.

These initial overtures reinforced my fantasy world of domination and penetration through anal ecstasy but, also convinced me that this arena was best relegated to the world of the sex industry professionals who must have had some special training or expertise unknown to my naïve self.

Fortunately, my libido was intact and the tape of domination and subjugation playing through my head provided ample fodder to lubricate and enhance my pleasure. One partner (and yes, I am a girl, and he is a male…but, I hate to say boyfriend, as sometimes a lay is JUST a lay!), though this man was working on all cylinders. After a thorough oral basting followed by some enthusiastic *******, my natural juices were predictably flowing and he had flipped me over for the deep thrusting from behind that he knew I enjoyed.

As he began to increase his rhythm he reached around and massaged my clitoris, covering his fingers with my natural lubrication. In a new maneuver, he then took his moistened finger and begin to first tap, then encircle the rim of my anus. This sensation was different and I responded enthusiastically…reaching to meet his urgent thrusting with an arching of my back. It felt different, and pleasant…

As I relaxed into the new sensation, he then slowly dipped his finger into my ***. This intrusion didn’t hurt at all, as I was thoroughly relaxed by his tender circling and tapping at the rim. It felt…different, and exciting. He continued to pound my ***** while inserting and probing my anus with his finger. It felt wonderful and I relaxed into this new and pleasant sensation. While still probing and wiggling with his right hand, he reached down and wrapped his left around my neck and shoulders…pulling my head into his, he leaned into my ear and whispered, “May I?”

I knew what he meant, and not even trusting myself to speak the words, I nodded…slowly but, without mistake...thinking to myself, “Please!” He first pulled his erect penis from my front leaving a vacuum where I was once filled, and then withdrew his finger…I was empty where I had been a center of pleasure but, not for long. Gripping his **** with his hand, he nudged the tip towards where his finger had been inserted just moments before. It began to slide in, he nudged, then pushed it in. It was only in a short bit of the way, but I could not ignore the feeling. It was not the gripping pain that I had previously rejected but, it was not comfortable. He waited, patiently, allowing me to get used to it then began to slowly slide in deeper. I relaxed and adjusted to this new sensation. He asked me, “Are you okay?” I really wasn’t sure if I was but, knew that I wanted to feel more. Again…I nodded.

He pulled out almost to the tip of his penis, and then sliding forward, finally pushed in all the way. He sat there, I adjusted to the shape of his penis in my backside and as I felt the fullness, the sensations I could not help myself, I began to slowly rock. When I did this, he began to slide in and out, never fully removing his **** but, always plunging it all the way back in. I yearned for those deep thrusts and circled my hips to accommodate his steadily thrusting ****. I felt new sensations, I was first so excited that I had finally breached my anal cherry but, conscious thought soon left, as I was overcome with this new and thrilling sensation. He moved, I moaned.

As my excitement mounted, he reached down and began to stroke my **** gently with light, feathery strokes…more of a tapping, then a stroke. And my climax began to mount, I thought I had *** before but, this was building deep inside me, from my lower abdomen all the way to the backs of my thighs, I could feel the climax approach and build. His tapping of my **** gave way to stroking and circling, as his thrusting in my *** became faster, and harder. It didn’t hurt more but, instead felt even more wonderful. I felt he could have pummeled me forever!

As I began to clench prior to my release, that pre-orgasmic stillness when all muscles clench, he released my **** and grabbed either side of my hips and thrust with more authority and urgency than before…all the way in and out…over and over. I clenched, and came….with a stifled moan erupting into a yell as every clenched muscle relaxed following.

He pulled his **** out, and came all over my backside before falling over me, wrapping his arms around me to pull me in. Stroking my hair and the side of my face, he gently kissed my chin. Looking me in the eye, he repeated the question, “Are you okay?” Finally…finding my voice voice…I looked directly at his eyes, smiled with a grin that covered my face and joy erupting from my eyes I breathed a firm, “Yes!”.

Thanks for reading!
CagedKitty CagedKitty
36-40, F
9 Responses Nov 27, 2012

Damn! that was a sexy story! Thanks for sharing

outstanding recount! i felt like i was right besideyou the whole time!

Fantastic story...well documented.

Great story very hot!

excellent story of your first time - whew!

That was Awesome! Thanks for the detail and the tips!

Great story. Thanks for sharing it. It reminds me of the first time I was allowed into a woman's backside. Fond memories.

Great story thanks for sharing :)

That sounds awesome. Wish it was me.