My Bookkeeper Returns

I gripped her upper thigh firmly with both hands and worked my inner index finger all over her wonderful slimy parts while Michelle bucked against it, voicing small plaintive, "oh, oh, oh" sounds every few seconds. Soon her rhythmic gripping of my hand became stronger and stronger. I judged that she wasn't far from going over the top. I waited for a moment when she relaxed her strong thighs enough after squeezing against me and then snatched my hands away.

She groaned in protest and sagged against the bed, her back heaving under the thick white robe with the breath of her exertions. "Oh, Peter!" she exclaimed, and then again after a deep breath, "Oh, Peter!"

I felt certain that if I repeated with a massage of her other thigh and its culminating hot juncture, she would get the orgasm she had almost achieved. Not my plan, though. I smacked her bum a couple of times, not hard, enjoying watching its jiggling softness, and said, "You're going to cum when I want you to, not before."

I returned to massaging her bum, taking pleasure in its soft, full cheeks and well-oiled crevice and working the pad of a finger around and around her anus. Again, she seemed to enjoy that attention, so after a few minutes I tapped her and said, "Lift your bum up, and spread your legs a little more." While she moved I took a pillow and a nearby cushion, and slid them under her hips. "Now relax."

She did, settling comfortably on the cushioning beneath her, bum raised nicely, very enticingly in the air, her wet centre open and exposed with its thick, smooth lips glistening. The robe had slipped off onto the bed, and she was now completely naked, and beautiful, and hot. Wow.

Returning one hand to continue kneading her bum, with the other I reached for the wicked-looking stainless steel dildo.

It had three bumps spaced evenly along one end of its length, the first being a small expansion at the tip with each successive bump increased in size for anal play, while the other end curved and terminated in a larger bulb perfect for g-spot stimulation. A great tool, with many successes notched (figuratively!) on it. Her bum was still plenty lubricated, so after sliding the cold steel dildo around to coat it with oil - she gasped and squirmed - I pressed the small end against Michelle's crinkled hole and applied pressure. She sucked in her breath, and tensed against it. I pressed a little harder, but heard a small sound like a whimper so I stopped. After a pause she said, her voice muffled by the pillow, "Peter, I don't know if I'm up for that, I've never had anything there before." She sounded embarrassed. I was surprised after her apparently-enthusiastic response to my finger rubbing the outside of her bumhole. I decided to push the point - not literally of course.

"Does it hurt, Michelle?"

"No," she admitted, "but it doesn't feel right. And it's distracting from all the other nice stuff you were doing."

"We agreed, though, didn't we Michelle?" I asked gently. "You were willing to do whatever I wanted you to do, excepting anything that hurt you. I want you to do this. For you."

I waited patiently for her response. When it came, it was preceded by an exasperated little grunt. Hmmm, maybe not so submissive after all?

"OK," she said, "impale me if you have to. But I'm going to have a lawyer for our agreement next time!" She gave a little laugh.

I spanked her bum lightly a few times again. "You behave, young lady. You're in a perfect position for a very good spanking. Now just relax, push out against it a little bit, and it will go in easily."

And so it did. With the first small bump of the tool inside, I began rubbing her glistening pussy again with one hand, bumping into her clit frequently, while I wiggled the steel dildo gently with the other, working its little bulb just inside her anus. It took a while, but soon the attentions at her pussy and bum had her pretty distracted as she began to moan and move again. I don't think she even noticed the second bulb going in, and it was her own excited bucking and squeezing moments later that forced in the third and largest bulb. I whirred my fingers on her clit while I slowly slid the tool deep inside her bum, all three bumps on it rubbing along her sensitive sheath inside. She gasped, and cried out, and gasped again, and began to go rigid as I wriggled hand and dildo around at her sensitive center.

And again I stopped, to her frustrated cry, and watched her breathing settle again, mouth open, face sagged deep into her pillow, as I rubbed softly on her sloping back, over her raised bum, and a little around her slick pussy. I gave the dildo a sharp little twist, and she sucked in her breath. "Ohhhhh! OK sir, you made your point. It's different, but it is pretty interesting." Then, in a much softer and less-flippant tone she said, "Thank you Peter. I will do whatever you want me to do. No more argument. But pleeeze, can you finish me off now? I can't take much more of this fabulous up-and-down agony, my muscles down there aren't used to this kind of workout."

"OK," I relented. "Flip over onto your back. But be very careful when you're settling your bum onto the bed. The impaler is staying in, part of it is sticking out of your bum, and you could really hurt yourself."

She carefully turned over as I removed the cushions from beneath her, and gingerly lowered her bum onto the bed, feeling the steel dildo pressing inside her. As she settled and I saw her naked front for the first time, I marveled at how beautiful she was. Her middle age certainly did not show in her full breasts, her smooth stomach, her narrow waist, her newly and neatly-trimmed pussy, or her strong legs. Stunning. The pearls just capped it off. The centuries during which they have been among the most prized of all jewels become understandable in an instant when seen like this. There is no sight more beautiful than a naked woman in pearls. As she looked up at me openly admiring her, she reached for my hand.

"You make me feel like such a beautiful woman." Her eyes glistened. "I haven't felt like it in a very long time. I know we're not going to date, don't worry. I just want you to know how truly grateful I am." She smiled softly, almost sadly, and drew my hand to her lips.

I took off my shirt and lay on the bed beside her, folding her into a soft bear hug and a long gentle kiss.

"I'm grateful too, Michelle. Being appreciated as a lover is almost better than the sex itself. You make me feel very fulfilled too. But," and I reached down and tweaked the dildo in her bum, "the show's not over 'til the fat lady sings!"

"Hey, I'm not fat!" She grinned and punched my shoulder gently, and then looked deep into my eyes. "But you can make me sing. Oh boy, you REALLY make me sing!"

She said she wanted to head for home, so to speak, but there didn't seem to be any point in rushing it. I reached for the magic oil again. She watched un-protesting as I raised it high over her, and aimed for her left nipple. Perfectly. Her nipple hardened against the cold drip that landed on it, and she sucked air through her nose. I wasn't as good at hitting her other nipple, but it hardened too.

As I slowly dripped more here and there over her breasts and onto her flat stomach, her breathing began to quicken yet again. I could feel her watching my face as I was intent on my drip-artistry, and then she reached to caress it with her warm hand. I put down the oil and kissed her again, long and soft, gently duelling with her tongue as I began caressing her breasts and stomach, spreading the oil around and delighting again in the silky-smooth softness of this beautiful woman. Her breaths became longer, and deeper, and she reached behind my neck and pulled me to her face as I worked nearer and nearer to her pussy. She made a little noise and sucked my tongue deeper into her mouth as I finally glided further down onto her pussy, taking more oil down to add to her own still-slick heat, and firmly cupped her pussy in my hand.

Remembering the success of our other time together, I had already decided to repeat my hand magic and help her to another ripping, squirting blast-off before taking my pleasure. I really did enjoy giving it almost as much as getting it. Without much pre-amble - she was already moving herself against my hand - I slowly sank a couple of fingers inside her. As she stiffened in pleasure against them, I could feel the hard knobs of the dildo in her bum move against the back of my fingers against her vaginal wall, and she stiffened more. This was going to be plenty good enough, I decided, I wouldn't need any of the other toys I had brought. I hooked my fingers into the fleshy pad of her g-spot, settled the Mount of Venus (what a great name!) of my palm against her clit, and began rhythmically squeezing and sliding my hand around.

She exhaled hard into my mouth, and I pulled back as much as her hand firmly clamped to the back of my neck would allow to watch her face and let her breath. She sucked in a long breath and held it, raising her pelvis to push into my hand and then lowering it against the bed, and I could again feel the dildo moving in her bum before she gasped out again. I imagined that she could feel it much more as she grunted and sucked air deeply, and rolled her bum on the bed.

It was obvious that she liked my trusty toy... notch up another one. I squeezed against her insides and wriggled my palm against her clit a few more times. As I locked my lips over one of her nipples and squeezed hard with them, her eyes rolled back and she grunted in a very unladylike way, when I did it again she cried out and stiffened hard off the bed, holding her breath again as I sucked the nipple firmly into my mouth.

I slowed the squeezing rhythm of my hand, trying to prolong her time on the plateau, but she was over-primed from our previous climbs that night and I miscalculated. Her ever-so-satisfying hot squirting and splashing through my fingers preceded her sharp cry by a second or two. With a practiced flip I pulled the protruding end of the dildo out of harm's way just before she crashed her hips onto the bed and pulled her legs up very tightly, trapping my hand between them.

She grunted out a prolonged, "Uugghhhhhhhh!!" before pulling my head down with great strength into a very hard, passionate kiss. I felt the quivering and rolling of her stomach muscles against my trapped wrist, and she made a strangled sound in her throat as still more hot liquid gushed out of her. Gawd, it was great.

I held her for long minutes as she slowly relaxed her legs back on to the bed, and sagged, and her breathing slowed, before deciding it was time to take my own reward. It wasn't going to take much, I was well-primed myself.

I nudged Michelle gently a few times until she became conscious of my intent, she was still pretty hazy. She kissed me again, weakly, and rolled over, raising her bum in the air again, giving herself to me, and rubbed my leg in encouragement. As she lowered her head to the pillow again I slowly pulled the dildo out of her bum, and she winced a bit as I did it... not the fun part. Then I positioned myself behind her, lowered my shorts, and slowly slid home into her sopping wet, blazing hot pussy. Not tight, but I felt my balls sliding around on her slick nether lips as I pushed in all the way, felt the heat, felt the little fingers inside her stroking me, and then felt her squeeze down against me. It really wasn't going to take much.

I gripped her soft bum cheeks and pushed into her as far as I could bury myself before gliding slowly back out. Fifteen exquisite, slow sloppy strokes later, when she reached between her legs and caressed my balls as I strained to hit bottom, I exploded, gushing deep into her the hot jism that had been building in my balls through hours of anticipation and excitement. I grunted, and gripped her bum harder, and squirmed against her, as the release exploded from me in a series of powerful pulses while I held my breath and the room seemed to go dark.

Then I lowered myself gently over her back to give her a grateful squeeze before rolling off to fold her into my arms. We both lay there, breathing slowly returning to normal, perspiration evaporation cooling our backs while our joined fronts stayed warm, soft, tenderly still exciting. She had her hand resting lightly on my cheek, and was murmuring very softly, perhaps thinking she was talking. I couldn't understand many words, but I thought I understood her intentions. I done good.

I had not planned an exit strategy, and realized I didn't feel like I needed one. As the soft, warm woman nestled in my arms drifted off to sleep, I let the pleasant darkness gradually overtake me too, though not before I had a semi-stiffy rubbing against her soft belly, imagining what we would do together when we awoke.