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I knew this was going to be challenging, though Ali had decided she really wanted to try and experience some new sensations. I looked at the vision before me and sighed, I was such a lucky man. I could not get enough of such a sexy woman, and we had talked jokingly about this for so long. Ali was knelt down on the bed in front of me, perfect firm naked ass stuck high in the air. Her hold-up stockings served only to highlight the flesh I was about to play with, and her firm, full breasts were barely contained in a lacy, quarter cup black bra, nipples clearly aroused and visible.
We had met an hour earlier, and it hadn’t taken long for us to fall into the bedroom and have an amazing fuck on the bed, Ali’s legs wrapped around my back as she cried out and came on my thrusting cock. But we both knew that this was just the warm up this time, and her flooded pussy was going to be stretched again before the day was finished. I knew I needed to take it slowly and at Ali’s pace, heed any requests, so she can fully enjoy the new sensations.
I slowly dribbled a light oil onto her upturned cheeks. The silky feel of her flesh under my hands was divine. I began to work the oil around, massaging her ass cheeks back, forward around, in and out, working the muscles under my fingers and slowly easing her cheeks around. Ali just groaned her pleasure as I worked on her gorgeous ass. Her rear hole was tight, puckered and inviting, and oil was dribbled around it but for now I stayed clear. Slowly my hands strayed onto the tops of her thighs, working around the flesh, in between and close to her smooth pussy so recently plundered by my cock. Back and forth, oily hands sliding easily over the smooth flesh but now working in towards the tight hole for the first time.
Lightly touching it, oil trickling around and down, teasing gently the flesh around it, tracing my fingers down below and on towards her pussy before coming back to rub around the tight ring again. Finally stopping and gently easing the tip, just the tip, of a slick, oily finger into the tight ring of muscle. Ali shuddered and I stopped, but Ali whispered, “Its fine, please, go on…. ” so I resumed my progress. More oil, the slickness helping the single digit ease a little further in until it was up to the first knuckle. Pulling it in and out a little I worked on making the entrance to her rear just a little more easy, before working the oily finger a little further. Now I could feel the tightness of her virgin ass as my finger slowly worked in and out of her ass, sinking further and further, gently penetrating her and filling her up. Ali’s breathing was shallow as she struggled to accommodate this, to enjoy this and I leaned over and whispered my question, “Still OK?”. She nodded, smiling, and mouthed, “Better than I thought… so far… but you better not stop now…”
I took her at her word, and began easing my finger slowly in and out of her now slick ass. More oil and the finger slid easily into her tight tube, bringing groans from Ali, but not of pain almanbahis şikayet or distress, so I worked my finger further in until I was using the full length, sliding it around in her tight rear hole and working the ring of muscle at the entrance. Taking plenty of time and oil, her ass was now taking my finger easily, and unconsciously Ali was starting to rock her hips slightly to make full use of its short length. After a while I eased the single finger out to its tip, then sat the tip of a second finger alongside the first and gently pushed at the well lubricated entrance to her ass. Ali squealed a little as the tips of two fingers widened her ass a little more than before, breathed heavily and settled back on her elbows. With my free hand I worked her cheeks again, all the time slipping the tips of two fingers in and out of her. I dipped the fingers of my other hand between her fantastic thighs and along her pussy lips. They were soaking, parted and leaking her sexual honey in a heady mix with my own cum from earlier. Her parted pussy lips were engorged with blood as her excitement was still high, so I concentrated on the new sensations, and using plenty of oil again worked two fingers in to the first knuckle. In and out these two digits went and slowly but surely they worked a little further in, stretching the muscles of her pert ass and accommodating my fingers more and more easily. Her ass felt slick and tight, ready for my next trick, ready for something a little longer…
Ali’s ass glistened with the oil liberally spread across it, her cheeks taut and spread as my two fingers worked steadily in and out and increased their penetration of her ass. Finally the two were embedded in her as far as the first one and Ali was beginning to pant a little as I worked the oil onto my fingers and steadily fucked her ass with them. For her part she worked back and forwards onto my fingers, reaching under herself to tickle her pussy with one hand as her ass took my fingers ever more easily. I leaned forward and stroked her left nipple lightly as I whispered, “More?? Are you ready??” Ali flinched as my fingers pulled gently at her erect nub of flesh, her nipple betraying her aroused state. She just nodded… I stopped my playing with her nipple and eased the fingers to the entrance to her fantastic, slick ass. As my fingers left I slipped the first, small bead past the ring of muscles, lodging it just inside her. Tugging on it, feeling the pull as it stayed inside her, I fed the second, ever-so-slightly larger ball in and the first went deeper. Ali grunted a little as I fed the third one in, again a slightly larger bead, and now her sexy butt had three beads filling it, each one slightly bigger than the other but none of them as wide as the two fingers she had so recently accommodated.
I tugged at the beads, widening her anus a little with the last bead, then letting it slide back. Again and again, just playing the muscles at the tight opening of her perfect butt, the sheen of the oil on her tight cheeks making almanbahis canlı casino the whole of her ass glisten in the light. Finally, letting the third one settle back I eased the next one. Ali gasped, “No… ooohh.. nernoooo.. oh god… yes..” as the fourth bead, larger still, popped into her increasingly full ass. The fifth one was easy, Ali almost expecting it now as the widest bead she had taken slid easily home. I rolled her cheeks around leaving the beads in place. There were more, two more, but these would wait for another time as the length of the string and the width of the last two might spoil what was clearly a good feeling. Ali was groaning beneath me as I played with her cheeks, pulling them apart, pushing them close, fondling the firm, shiny flesh and enjoying the sensations under my fingers. Sliding a finger down between her cheeks, past the fullness of her rear onto the flesh between her ass and pussy then finally, dipping between overflowing pussy lips. Even as I touched her clit…. Ali exploded, falling a little forward, as the sensations overcame her……
As her orgasm took hold I started to tug the beads from her ass, knowing the sensation of these easing out would heighten her feelings. Her orgasm seemed to go on for ages, as each of the five beads were popped out of her well oiled rear. As the last one came out Ali shuddered, the last throes of her climax over. I used a little more oil and gently stroked her cheeks, thighs and back working the muscles again, lightly touching the flesh and easing her back down from her high. I looked over this incredibly sexy woman and took in her fantastic ass cheeks, the recently plundered rear hole still a little wider and shining with all the oil use. Her long firm legs still covered in the fine black nylon of her hold-ups and her heeled, polished black shoes setting them off perfectly. Her full, ripe breasts hung within the confines of the quarter cup bra, her aroused nipples erect and prominent even without much playing. Ali was looking back at me as I smoothed my hands around her body, working again on her ass, opening and closing her rear and getting it ready for the final time today….
“Thank you, that was so much better than I expected…”, she whispered, “I think I would like to do something similar again some time!”
“Good, I have one more surprise for you now, one which I hope you will like and I know I will.”
I reached to the side and found the small, starter butt plug. Flexible silicone based, it was only about 5 inches long and not too wide, but perhaps a little wider than the last bead. The conical shape was lightly ridge, and I oiled it up before inserting just the tip into her waiting rear. Ali didn’t flinch this time, easing back as if to try to suck it in more quickly. Toying with her ass, teasing it, sliding the tip in and out, almost fucking her rear with the plug but slowly, ever so slowly I was working more and more of it into Ali. As she realised what was going on she looked back at me, raising almanbahis casino her eyebrows in question. I nodded, knowing she was asking me if I thought she would be able to take it. She would, and I coated the last inch, the widest part, with a little more oil before turning it slowly around and putting a little more pressure on. Ali’s breathing quickened but she held still as the widest part stretched her anal muscles a little more than before, then finally it popped in and the flange of the plug nestled sexily between her glorious ass cheeks. Ali wiggled her ass at me, pleased she had taken it all and seemingly enjoying the sensation of having her ass full.
I was now ready myself, and my cock was back to full hardness after its earlier exploits. Oiling it a little, I then started to play with Ali’s pussy lips from behind, sliding my finger up and down without really penetrating, but all the while collecting her glorious juices on my finger. Reaching forward I let her taste some, licking my finger clean as if giving my cock a seriously sexy blow job. I edged forward onto the bed and positioned the head of my cock ready, then slid it up and down between those pussy lips again. Ali realised what was about to happen, and looked startled, but I pressed gently forward before she could scoot away. An inch of my cock found its way easily between her lips and into her waiting pussy, her cunt. God this felt tight, the constriction given by her full ass was playing havoc with my cock, already teasingly close on the sensations alone. Ali relaxed, and I slid a little further in, feeling the plug as I did so. Her pussy was tighter than earlier, and the pressure on my cock was greater as I worked slowly in and out, penetrating deeper each time.
Finally I filled her completely, and Ali pressed back to make sure before squealing surprise as the motion pushed me onto the flange of the plug. The plug and my cock moved inside her, I felt Ali tense and shudder with a mini orgasm at the unexpected nature of this. Slowly I pulled out a little before thrusting gently back in. Each inward thrust ended with a push on the plug, driving it into her ass as her pussy was stuffed full of my cock. Ali was writhing now, and I strove to hold onto her back, her waist, her hips, as I reached a steady rhythm, gently pounding away at her naked pussy and hitting her plug-filled ass each thrust inward. Finally I could feel I was getting close to my own orgasm and I sped up, Ali responding by thrusting back to meet me and reaching under us both to flick at her clit as she hit an enormous orgasm. She clenched hard around my cock and the plug as the waves swept through her, and I couldn’t stop. Finally I came, spurt after spurt of my cum filling her tight cunt, her gorgeously full pussy as I pulsed time and again into her waiting folds…. Finally we collapsed, my cock still embedded in her full pussy, the plug still pushing against me and her as I lay on her back, stroking her neck and whispering, “Fantastic, that was amazing, you were amazing…. I came so hard, and you seemed to like it too??” I was still checking Ali was OK with what had gone on, but I needn’t have worried. She turned and smiled, nodding in agreement and said, “Mmm, I can’t remember ever being so full…. but do you think I could be fuller??”
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