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She took her time and pushed slightly, breaching my opening just barely with her finger tip. My head back and my eyes closed, I couldn’t help but let out a warm "Mmmmm".
"I had no idea you'd be into this." She said quietly. I opened my eyes to see her smiling and staring at my ass with concentration. "But it's so hot!" she continued. That was it. All my worries were now gone completely, knowing that she was enjoying what we were experiencing together.
As my thumb continued to slide around her clit, her middle finger continued to probe further into my ass. Firmly now, she had begun inserting more and more. She curled her finger slightly and started pumping in and out. Then suddenly without warning she stopped. She slowly removed her finger and continued circling the hole as she had done in the beginning. With her free hand she took my hand off her body and moved it over to the toy we had lying on the bed between us. Without words, I looked in her eyes and she gave me a slight nod with a smile. I took the glass plug in my hand and shuffled my legs open even wider. I noticed her move briefly, I suppose to wipe her finger clean with a Kleenex from the nightstand. But I was far too engrossed in what I was now doing to say for sure what she was doing at this point. She laid down beside me now and caressed my chest while I kissing my neck and cheek. It felt amazing in tandem with the glass now circling my anus.
I moved it slowly at first and somewhat copied what she'd done with her finger. As I started to push, I realized even the tip was thicker than her finger and when it breached my hole I closed my eyes and sighed. It actually slipped in quickly for a moment since the glass was frictionless with the lube. I removed it and repeated the motion. Slower this time it started to slide in. Bit by bit, I was pushing up towards my stomach. As it got wider and wider I could actually feel my anus stretching. Trying my best to relax I kept pushing ever so slowly. It was only half-way in when I stopped and had a moment when I felt I had to ‘reset’. So I squeezed my ass tight and pulled it out completely. By this time Jenn was now kissing my chest, licking my nipples and stroking my hard penis, but still quiet and supportive. I still had my eyes closed, but I heard her whisper "Please don't hurt yourself babe." After a few hard squeezes of my empty anus, I was ready to continue.
With a quick breath, I pushed on my opening with the toy again and it made a much smoother entrance this time. I started gradually getting it further and further and now I could really feel the stretching. I had to start slowly pumping it in and back out slightly, then further in and back out slightly. I continued like that as it got closer to the thick base. There were a few moments where I had to hold it in place and take a breath. It was starting to become a really intense feeling as I tried different motions to easy the stretching. I twisted it in my fingers while I lightly pumped it in and out. Then I figured I had to just go for it, so I took one last breath and firmly but slowly pushed for the goal. It was an odd combination of pain and pleasure when I felt my anus expand to what seemed to be its limit. Then suddenly, the toy got past its widest part and just popped in completely. It happened so quickly that the tip of the glass hit my prostate and I gasped loudly. My eyes shot open and I looked at Jenn. "It’s in." were the only words that could come out of my mouth.
"No way!" She said as she jumped up on her elbow and looked for herself. Her eyes wide, she looked back up at my face with a big smile and then turned back to quickly swallow as much of my cock as she could. With my rock hard member deep in Jenn’s mouth and a solid glass plug deep in my ass, I was in complete heaven.
As she moved her mouth around my cock she motioned to take control of the toy. I removed my hand and she began to gently twist it with her fingers. It was no longer touching my prostate (it only did that at the initial entry), so I whispered for her to push and she did. The toy seemed to be just barely too short to touch the prostate while sitting in naturally, but as soon as she added some slight pressure I could feel my insides rejoicing. I couldn't believe the experience, the pleasure. As she continued to twist and push and pump the toy I began squirming in ecstasy. All that and at the same time she had me in her mouth. It was unlike any blowjob she had given me before however. It had always been her specialty in my opinion, but this time she must have been concentrating more on my ass than my cock as she was simply holding me deep in her throat for the majority of the time. Since she had no free hand to use she would pull her mouth up the entire length of my cock and then immediate slide it back down again, practically swallowing it entirely. She is an absolute expert and it was absolute bliss.
While I continually felt the pressure on my prostate and the mouth around my cock I started to lose all control. My body was sweating and I started writhing from the sensations. I heard her moaning as she could tell I was clearly close to orgasm. I'm sure it was only seconds, but it felt like an eternity of paradise. Then it came to an abrupt end when I simply had to let go and erupted in her mouth. As I was letting go, pumping spurt after spurt in her throat, Jenn was pushing hard on the toy giving my ass all it could take and applying the greatest pressure my prostate had ever had. I could hear her moaning again as she tried her best to keep my cock deep in her mouth with my hips bucking and my cum flowing in her throat.
When it was over, she released the pressure on the plug, but kept my penis in her mouth a while longer. She continued to moan while her head slowly bobbed on my shaft, waiting for it to soften slightly. When she was ready, she slowly slid her mouth up my penis, careful not to spill any cum along the way and kept her lips tightly closed around the tip as she swallowed twice. At this point I had my eyes open, watching the master at work. And in the aftermath, I concluded that it had been by far the most intense and amazing orgasm I had ever had in my life to that point.
Of course there was still the matter of the plug in my ass. As hard as it was to get in, I thought it could be just as hard to get out. Contrary to that however, it popped out quite easily after a short push of my muscles and a slight tug on the base. While it did stretch my anus to its max again on the way out, it was far less painful this time and by this point felt quite relieving to get it out.
I simply reached over and put it aside on the nightstand and then lied back in complete relaxation. Jenn was again lying beside me caressing my chest as she did earlier, and she kissed my chin and said "Thank you for sharing that with me."
I looked in her eyes, amazed at this wonderful woman and said "No, thank you!"
I started to glide my hands over her body and ended up between her legs (of course), where I discovered just how much she had enjoyed the experience. She was literally dripping down her legs from her own excitement. I pulled my glistening fingers back up to my mouth and licked them clean. She gave me a coy smile and grabbed my face to kiss me deeply. I rolled on top of her and started grinning.
"Well I did it." I said. "So you know what that means… now it’s your turn."
The End.
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