Two nights before my unexpected experience at school Sadie led me through the pathways of anal sex. Remember she had already directed my fingers in that direction as a form of stimulus, and that night I was busying myself with that pleasuring. I was happily applying my tongue to her engorged clit, enjoying the sounds of her excited breathing. My fingers were spread so that while my index finger dallied in her vagina, with the subtle movement she had guided me into, my third finger was gentle teasing in and around her asshole. The difference in tensions of the two entrances was so intriguing. My cock was aching, longing to get involved in the action when Sadie touched my head and I looked up at her raised, impassioned face.
"Would you like to go in there?"
"Here, of course." I said, wiggling my index finger.
"No, the other one. Where you're working right now."
Put my cock into her ass? Was that allowed? But wasn't that how I'd felt about using my finger there? "Won't it hurt you?"
"It did, when it first happened---but that was---Well, I can take it now. Like to take it now."
And she sat up and turned her body so she was kneeling forward, her hand reached back, closed around my swollen cock, and drew me towards her raised ass. She placed my penis head against that tight hole, then lowered it to her vagina. "Once in there and then out."
Puzzled and uncertain I slid my cock deep into her vagina, thrilling at the sensation of it. "Now out---all the way out."
Regretfully, I retracted. "Now, you're nicely lubricated to enter." And she placed me back at that tight little entrance. "Now, just gentle pressure."
I just couldn't imagine my generously sized cock getting through that tiny opening. But with my first push I was an inch inside her and I heard her deep sigh of pleasure. As a pressed tentatively her hips suddenly thrust back and I was plunged into that deep mysterious passage. The forbidden place, I would have thought.
But God, it felt deliciously tight as I began thrusting back and forwards and Sadie's hips responded.
"Reach round to my clit," Sadie grunted.
I put both arms around her, hands spreading over her heaving belly and slid my fingers down into the moistness of her labia, where her little button was as erect as I'd ever felt it. I began strumming my fingers over it while continuing the deep slides into her ass. The excitement of it was making my balls ready to explode and I listened more attentively to her rapturous breathing, getting to recognise the sound of approaching climax. Sharp breathing quickening, before becoming more vocal, a husky guttural sound that rose to almost squeal pitch on an 'Ah' sound.
She wasn't quite to that yet, and I was enjoying this new experience, so different from the vaginal penetration. It was like having my erect cock pass along a series of tight rubber rings, with the first one the tightest, only everything was much warmer and more active than that.
Really excited now, I plunged full depth while my fingers flickered on her clit. I was about to burst. I humped faster, harder, forgetting everything about care, just riding on a wave of
exhultation that I could cum in this new found lobby.
And it was just then that Sadie's grunted,'Ah' began, repeated, higher pitched as she neared her own climax. She threw back her head and I lay over her back as I pushed deeply and she hissed, "Oh, yes, Jack. Aaah." Knowing she was there I was able to let go and that moment of wild release as I spurted up inside her was like no other I'd had up to that time. She, for her part, was crying out more than she had ever done thudding her buttocks back against me. My climax seemed to go on and on.
At last we collapsed together across the bed, sweated and
complete.
"If you ever try that with any of the many conquests you have ahead of you, be very careful. I'm already stretched there, but first time, no matter how much your fingering might have encouraged her,
can be difficult."
"Was yours?"
"Yes, but we won't talk about that now." She turned her face to mine. "Let's talk about your next conquest. Anyone in view?"
I told her there wasn't and that was the truth but just two days later a real plum literally dropped into my lap. And it just showed how easily word of mouth can create your reputation.
In my earlier story I mentioned how much I was attracted to the blonde Miss Orry, our class tutor at school. I had always reckoned she couldn't have been more than fiveyears older than me. Maybe twenty three, twenty four. But such a trim figure, and she always wore thin sweaters that emphasised an elegant looking bust. Not large, but surely delectable.
Anyway, ever since my sessions with Jan and Mandy I had the feeling that Miss Orry had been giving me long inquisitive looks. Well, last session that Friday our group had a mixed gym session in which we did some circuit training and I was surprised to see Miss Orry come in and take over from Mr Martin, our usual instructor.
"I didn't know this was your area of expertise," I said to her as we crossed over between apparatus.
"There's a lot you don't know about me," she said, which could have been innocent, but the look that went with it intrigued me.