please.”
And I do. I actually stop protesting and I do it.
Dan walks behind me and crouches. I flinch as he caresses my left buttock, the red stripes still making themselves felt despite his gentle touch. But the pain is nowhere near as severe as I imagined it would be.
“Reach back with both hands and hold your butt cheeks apart if you would please.”
Ah, so polite. Wordless, I do as he asks. The slick coolness of the lubricant is oddly pleasant as he squirts it directly onto my exposed anus. I suppose he must have had that in his pocket too, though I don’t ask him. I’m too concerned right now with the unsettling sensation of having the lube worked into the delicate skin around my arse, and even inside the rim. I gasp as he slips one finger in, swirling it to smear the goo all around. He withdraws his finger, only to replace it with what I assume is the nozzle of the tube. He squeezes a generous amount directly inside me, and I squeal.
“Wimp. That didn’t hurt.”
I clench my bum in automatic self-defense, consciously loosening the tight muscle as he places his fingertip at the entrance again. I don’t want to resist, and I’m oddly reluctant to attract any fresh censure, no matter how gentle. “No, Sir. I’m sorry. It feels odd though.”
“Odd nasty or odd nice?” His words are accompanied by the penetration of one well-oiled finger, sliding easily inside my bum.
“Oh, Sir.”
I can’t help my startled moan, and he takes advantage of my apparent acquiescence to finger-fuck my arse. He isn’t rough with me, and is very deft about it, working the sphincter open to accept his presence more readily. I have to admit, he does seem very good at this, and he was right about my body accepting what’s happening. It feels strange, and distinctly humiliating, but it’s definitely not painful. Well, not yet. I start to revise that view as he inserts a second finger alongside the first. Now it’s tight, I feel stretched, less comfortable. Hurting. Getting scared.
“Tell me, Summer.”
“Tell you what, Sir?”
“Tell me.”
“It hurts, Sir. It’s scaring me now.”
“We slow down then. You were okay with one finger, right?”
“Yes, Sir. One was fine.”
“Like this?”
My body relaxes immediately as he reverts to just one finger, sliding it deep inside me and out again, each thrust hard and strong but no longer painful. I’m amazed, it was so easy. All I had to do was tell him.
“Okay now? Does that feel good?”
“Yes, Sir.” And it does. Incredible though that may be, it really does.
He shifts, reaching around and under me to strum my clit with his other hand. I groan my appreciation as my orgasm begins to unfurl. Helpless to resist, my pussy spasms in response as I lay my cheek flat against the rug under me. Dan takes that as his cue to up the ante once more, and slides that second finger into my arse again. This time, though, I’m fine. Bolstered by Dan’s quiet, confident efficiency, I’m even managing to relax and though it’s still tight there’s no sense of panic now. I gasp, but a couple of well-directed flicks across the tip of my clit soon restore orgasmic order. Moments later I’m climaxing hard.
Dan continues to thrust his fingers into my bum until the final waves of my release settle. He then pulls out, but only for a moment. Within seconds the cool hard surface of the butt plug presses against my now unresisting arse. It’s cool, but smooth, and less wide than his two fingers had been. It slides into my well lubricated and loosened arse with remarkable ease. My ring of muscle tightens around the narrow section, holding it in place. Dan circles my bum with his fingertip, nudging the protruding part of the plug to cause it to move inside me. I’m intensely aware of it, of each rocking, swirling motion. I groan, sinking my fingers into the deep pile of the rug. Dan gives the plug a couple of experimental tugs to ensure it’s not going anywhere. Then he stands
Jan (ILT) J. C.; Gerardi Greenburg