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Ron's toys	By : sandman-nobody Category: Kim Possible > Het- Male/Female Views: 93308 -:- Recommendations : 4 -:- Currently Reading : 9
Disclaimer: i do not own Kim Possible nor am i gaining any form of money/payment for this fanfiction

Chapter List
- 9
- 10
- 11
Tag(s): Anal, Anal-Fingering, Fingering, Reluctant-Orgasm.
Girl(s): Ann.
Toy(s) Sleep pen.
Word Count: 7865
Chapter 10 – To Do The Things I Do
We laid like for some time, neither of us caring about the mixed juices staining the bed. We were both sweaty, but it was still wonderful.
My hands, ever playful, happily cupped her breasts. Not explicitly sexual, they still kneaded the womanly mounds. Enjoying the soft texture and gentle weight. Ann didn’t seem to mind, lazily smiling whenever I did something she enjoyed.
Ten minutes must have passed before either of us made a move. Ann being the first, my still hard cock slowly grinding between her cheeks must have finally peeked her attention. Eyebrow raised, she took one look between us only to appear surprised.
“You are in a mood today.” I could only guess at what she meant.
Even after cumming what felt like a life time of semen, my dick was still as hard as when we’d started. The first taste of a woman in too long, I was far too starved to settle for one orgasm. Rather than point out my teenage virility, I had to smile. One that she just rolled her eyes at. Turning around her lips returned to mine. She seemed willing enough to try another round. More than happy to reciprocate, my fingers ran along the curve of her butt distracting me from the passion.
Ann belonged to James, legally and emotionally. She had chosen him to be her partner in everything until death do they part. There was nothing I could do about that. He was her first lover, her first husband, had given her her first child. And much more. I had given her another first today, one she had enjoyed greatly. But part of me still yearned for more. Just one more stone to even the scales.
“James?” she mumbled past my lips. But I couldn’t answer.
Despite the fact that I wanted nothing more than to forget about that damned night, my mind drifted to my evening with Shego. More specifically, to the way it had felt slip inside the tight hole of her backside.
As horrible as that night had been, that one part stood apart. And I couldn’t help but wonder how Ann’s might feel in comparison.
“Hey,” I started. Pulling away, my ‘wife’ was still confused. No doubt curious as to what could be distracting me. Turning her eyes in my direction, I tried to think about how I should even say this.
“Um… okay, ah. How would you feel about trying something… a little different?” I phrased the question as innocently as possible, but something told me she could still see I was nervous. Probably because she outright pointed it out.
“You seem nervous,” Though rather than suspicious she seemed more amused. A coy smile playing in her lips. Scooting back to get a better look at me, she laid on her side, propping her head on her palm. She smiled playfully. “What did you have in mind?”
If anything, her knowing I was nervous only made me more so. Putting on a strained smile, I continued to struggle, unsure how a husband was meant to ask his wife for backdoor privileges. As experienced as I’d become in the past few weeks I’d yet to encounter this subject. Finally, taking her hands in mine I decided to just say it.
“Okay so… keep an open mind,” I started. To which she just giggled, no doubt even more curious. I couldn’t help but laugh with her, groaning at my own lack of ability to communicate.
“Our sex is… wonderful,” we both couldn’t help but laugh at that understatement. “And I think we’ve both agreed that we enjoy each other’s mouths just as much.” Again she agreed, patiently nodding her head. “I was just hoping we could explore… other areas,” Waiting for her reaction, she just nodded again. Doing her best to keep from frowning.
“I still don’t understand,” she ducked her head. Running her hand down my chest, she tried to give me confidence. “Sweetie, whatever it is just tell me. I’m happy to try anything if it makes you happy…” she paused, a slight wrinkle forming in her brow. “Within reason.” She added, just for safe measure. I could only imagine what she was thinking. Then, realizing my hand was still fondling her butt, I decided it would be easier to show rather than tell.
“Just… for example…” I trailed off, slipping my fingers between the crack of her cheeks. Her expression curled, but it wasn’t until the tip of my finger brushed the wrinkled button of her backside that her eyes lit up with realization, only to flinch back. I waited for her response.
“Oh!” she gasped. Taking a moment, she just blinked, her wide eyes drifting off in thought as she considered what I was really saying. “Oh,” she repeated, this time a bit less startled. Though she had yet to slap my hand away.
She stayed like this for a while, not really blinking despite the exaggeration in her gaze. Finally, after what seemed like her hundredth deep breath, her blue eyes returned to me. Looking more conflicted than anything else. “That is… certainly adventurous” She acknowledged, though I couldn’t be sure if that was a good thing or not. Again she fell silent, but took the time to search my face. No doubt wondering the same as me. What the hell was she thinking?
“Can I ask what inspired this change?” She chose the words carefully, I could tell. I did my best to hold her gaze while trying to think of an explanation.
“Well, I’d be lying if I said this was something… new.” This earned a sharp look of surprise. “Um, but I guess I’ve done my best to hold myself back.” And it wasn’t until the words left my mouth that I realized how true they were. But rather than dwell on this revelation, I forced my attention on Ann, who appeared stricken at what I’d said.
“James!” she gasp, almost hurt, “you know you can talk to me about anything, don’t you?” The last part came out small, worried. The fact that she thought her husband was hiding something this important from her was no doubt scary. There would be ramifications for my actions, I knew that. But by then I would be hidden away atop a mountain for the rest of my life.
“I do, and I’m sorry,” I apologized. “That’s why I’m telling you now. Would that be something you’d be willing to try?” and that was the real question.
Ann took a deep breath, her plump bottom lip falling between her teeth. Glancing away, she thought for a moment before finally answering. “Medically speaking, it’s not very hygienic,” she started, vocalizing her thoughts. “Isn’t that supposed to hurt?” she asked. A fleck or worry taking her tone.
“I’m just asking to try,” I tried to reassure her. Weighing the words in my head, I finally decided it was worth it if it eased her fears. “And I’ve… done some research. So that should help it go smoothly.”
It was a gamble, but it was the best I could do without outright saying I’d done it before. Once again Ann appeared shaken, no doubt picturing her husband looking up pornography on top of everything else that had happened tonight. Finally she just shook her head, a smile fighting its way onto her lips.
“Remind me to avoid your search history,” she murmured listlessly. And sighing one more time, her eyes turned toward the bed, before flicking back toward mine. Tight and unsure. Finally, chewing on her lip, she muttered the one word I had been waiting for.
“Alright…”
It was quite, and nervous, but underneath I’d swear there was something close to excitement shining through. Nothing could stop the rush that swept through me that moment. Seeing my sudden exclamation, Ann immediately held up her hand, still shift nervously on the bed. “But I need a minute!” she quickly demanded, shooing my hands away while she crawled off the bed. I had a wonderful view of her pale rear before she stepped onto the floor, nervously tucking a strand of hair behind her ear.
“Stay here,” she ordered, her voice firm. And dare I say, a small smile curling her lips.
I was both surprised and delighted. Even going so far as to roll onto my back, arms comfortably tucked behind my head. Seeing that I would do as she said, Ann made another nervous expression, but forced herself to march across the room and into the adjoining bathroom. Stepping inside, she stole one last glance in my direction before closing the door.
A few moments later, the sound of sink being run could be heard. But other than that, I could only wonder what was happening on the other side of the door. Finally given a few minutes alone, I found my mind trailing back to the words I’d just said to Ann.
‘I’ve been holding back,’ why did that resound so solidly as soon as I’d said it? But even asking that, part of me was already well aware of the answer.
I guess I’d always sort of known. In a way. A word here, a feeling there. It’s just the way I was raised. To never speak up. To keep the peace. I’d gotten so use to the world being against me that I’d forgot what it was like to even want.
My relaxed expression darkened, just a fragment of the anger I knew had been building inside of me coming to the surface.
I keep blaming these things I’d found for my decisions. But at the end of the day, I needed to recognize that these desires, these cravings that have been driving me crazy over the last month… maybe they have always been there. And it’s just now that I have the power to make them reality that I dare acknowledge them.
My thoughts didn’t grow any more positive from there. Plagued by the reality of my own character, I almost forgot about the beautiful, nude woman in just the other room. But just like her daughter, when the door opened and I saw her, all the dark things in the world just seemed to blow away. Leaving only her, and me. A world of our own.
“Okay…” she smiled, a nervous light burning in her eyes.
Slowly making her way towards the bed, I spotted a bottle in her hand. She sat on the very edge of the mattress, eventually creeping close enough to hand it to me.
“You’re the expert,” she shifted next to me. I could her the joke under her nerves. “How do we, um, start?” I decided then that enough was enough and sat up to touch her face.
I kissed her before she could say another word. Neither passionate, nor lustful, it was slow, gentle, and most importantly, full of the honest love I felt for this woman. Words would do nothing to calm her racing heart. Nothing I could say anyways. If nothing else, I had to use my emotions.
My efforts seemed to work. At least somewhat. And when I pulled away I was relieved to see a smile replace tight line her lips had been.
This was important to me. But more than just because I was getting something James had yet to claim. Sure, that was a bonus, but even more important was that it was Ann, and this was a memory I would get to have of her after I was gone. Of course, I was excited to try this kind of sex again, but not if it meant making Ann uncomfortable. To me that wasn’t worth it.
“Relax,” I tried to tell her. Taking a deep breath, I watched and waited for her to look at me. When she did, she was fairing much better than the minute before. Even reaching for my hand to hold.
“We’ll go slowly?” she asked, though it held the tone of a command. I nodded my head nonetheless, easing her back onto the bed.
Setting the bottle of lotion beside me, my hands returned to Ann’s body. Demanding her lips, I went to work restoring the arousal that I’d worked so hard to achieve. Back on the bed, we cuddled next to each other making out like a couple of teenagers.
I purposefully kept my hands far away from her rear, keeping them busy with her breasts instead. The time for that would come soon. This helped in the slow motivation, pinching her nipples the way I knew she liked. And soon, I could feel a small bit of her arousal return to tighten the tips of her breasts.
I wanted her to enjoy this, I wanted her to look back fondly on today, and on me. Even if she never knows who it actually was who spent the day with her. With that in mind, I finally reached back for the bottle, squeezing a generous amount onto my middle finger.
“Tell me if I need to slow down,” I offered, reaching for the wide curve of her hips. Pressing her face into my neck, I felt her nod. I took this as her permission and easily slipped my finger between her cheeks and towards the tight opening of her rear. Feeling me touch the tender space, she frozen in my arms, relaxing only after the digit was safely inside.
She didn’t make it easy, unconsciously clenching down to fend off the intrusion. Against the blunt tip of my finger, I found myself cautiously applying more and more pressure, trusting the ring of muscle to give before there was any real pain. And it turned out I was right, slipping through in an instant. I think both of us were surprised to find my finger suddenly buried halfway inside her virginal cavity. A hot sigh broke against my collar.
“Okay?” I asked, doing my best to hold still. I knew there couldn’t be any real pain, but emotional stress was just as important. Finally, Ann nodded her head. And then went on to surprise me by reaching for my lips.
Captured in a sudden kiss, I quickly understood and returned the gesture. Keeping Ann’s mind adequately occupied, I began to slowly saw my finger in and out of her rear, doing my best to make the opening loosen to a comfortable state.
I swallowed a small grunt coming from Ann, feeling my finger sink deeper into her anus. Unable to help herself she pulled back, gripping my shoulder for support. Her features screwed up adorably, no doubt trying to grow use to the alien sensations. She couldn’t help but squirm, rolling her butt against my hand.
“It… doesn’t hurt,” she finally decided. Though I could tell she found the situation less than pleasant. I just nodded my head, keeping my eyes on her face before attempting another deeper stab. Once against she grunted, eyebrows drawing together. Testing my finger against the smooth wall of her insides, her eyes widened along with her mouth.
Another small gasp.
“It’s certainly odd though.” Retaking her position against my neck, I casually stroked the back of her head before asking.
“Are you ready for another finger?” my question seemed to exhaust the older woman. But after a few seconds, she nodded her head. And I pushed on. Without hesitation.
Feeling her around my fingers only made me that much more anxious to feel her around my dick. Despite the fear and tension we’d had to work through, I was still just as hard as when we’d been comfortably cuddling. I’m sure she could feel me, grinding against her belly. I could only wonder if she felt my size and imagined it where my fingers were now.
The second finger was both easier and harder than the first. With one already inside of her, there was much less resistance to fight against to get the digit inside. But at the same time, this was the point that she would feel pain of being stretched, and her grip on my shoulder changed accordingly.
Fingernails sank into my flesh, sharp and stinging. Bearing with it, I did my best to calm her. Waiting a few moments for the sensation to grow less acute, I finally began to work the two deeper, feeling the right ring of her anus strain around me.
One might think, caught in this torturously slow pace that I would get bored. Exasperated even. But in all honesty, this was fascinating. Even putting on this mask, I never once though I’d be put in this kind of position. One of power.
I was just a teenage boy. Next to Ann, a mature and adult woman, it was almost impossible to imagine me having anything to hold over her. But that was the only way I could see this situation. Me gently leading her through this alien experience. I guess when it came to age, new was still new.
A long groan sounded off my chest. Shifting on the bed, her hips pushed away from her body. An unconscious move, the effect spread her cheeks, making my intrusion just a bit easier to handle. Which was good, because I’d hardly moved and she already seemed to struggle.
“Keep going,” she managed. Holding her breath against the pain. Despite her discomfort, her tone was surprisingly strong. A testament to the iron will that ran through the mother. Feeling an odd spark of pride for the woman I loved, I did as she asked, driving the two finger as deep as they allowed. The motion was slow, possibly torturous. But when my knuckles finally bottomed out Ann allowed her tense muscled to relax. Most notably the one wrapped around my fingers.
“Tell me how it feels,” I murmured, listening to tight breaths caring the weight of her pain. Snapping open, Ann’s blue eyes looked up at me, seeming years younger than her age.
“What?” in pain and confused, she struggled to understand what I’d just said. With my free hand I touched her cheek, caressing the soft heavenly flesh.
“I want you to talk to me, tell how my fingers feel.” My tone falling deeper than intended, Ann seemed to see my intention, a stark flush consuming her pale cheeks. Sparing for a second, her eyes shut one again before opening to look at me through her lashes.
“It… hurts,” she started, breathless but doing her best. No doubt it was difficult to think proper with the constant onslaught of my finger spearing against her anal cavity. I kissed her brow, trying to encourage her. Taking a series of short quick breaths she tried again.
“It feels… hot,” she tried to rationalize. “Around my butt. Inside I can feel you moving around,” she suddenly stopped, grunting as my two digits struggled to form a tight V, still buried inside of her. Relaxing the exercises, she immediately slumped, the sweat building on her skin beating and dripping down to the sheets.
“I can feel you rubbing against the sides. And it feels… strange.” she was exhausted. Fighting to put up with what I was doing, Ann seemed ready to collapse. With this in mind, I debated my options before finally pulling my fingers free. She gasped, not expecting the sudden lack of sensation.
“Come on. Lie down.” I instructed. Confused, Ann followed my guiding hands, turning so that her stomach rested against the bedspread. Peeking over her shoulder, a single blue eyes watched me reposition myself on the bed. Moving to settle between her legs and right behind the generous hill of exposed bottom.
This was much closer to how it had been with Shego. Like this I’d have much more control, and the strain on Ann should lessen considerably. Apparently not a fan on change, Ann remained warry, watching me as I resupplied my fingers with a fresh helping lotion. Giving her butt my full attention, I reached forwards, spreading her cheeks to reveal the tight button resting just inches above line of her sex.
“James…” more of a moan than an exclamation, Ann took one look at me so brazenly eyeing her exposure and turned to bury her face in her arms.
“That’s my girl,” is smiled, marveling at how beautiful a picture this was.
A cheek in each hand, I squeezed the mounds, watching my fingers sink into the mature figure of her round bottom. I remember just yesterday, struggling to avoid glancing at the woman. What could possibly be worth more than this that made me think I’d ever be able to resist?
Keeping one cheek dramatically spread, my other hand traced down the line of her crack, stopping at the slightly swollen opening. Rubbing the cream around its rim, I soothed the irritation as best as I could. Ann’s soft groan seemed to signal a bit of progress. I took this as my sign to continue, replacing my finger back into her waiting opening.
I was happy to see me slip in without any issue. While still tight, I’d worked the muscle enough that it was able to accept the single digit without issue. Even Ann offered little complaint. A single cautious squeeze around my finger the only sign that she noticed me at all. Easing my hand to the small of her back, I applied the smallest bit of pressure and held her still while a second forced itself inside.
Again, easier than the first time. Soft and malleable, the sensitive skin wrinkled around my invading fingers. Taking a deep breath, I was eagerly moved to extend a third finger. Stretching the mother of three even further and finally achieving my goal. Her back flexed, and I could feel her start to squirm. But pinned against the bed, I held fast. And sure enough, slipping round the last digit her once small hole strained to reach its new size.
“Keep breathing,” I shushed, a muffled cry sounding from the woman’s other end. Still buried in her arms, I could only imagine the pinch expression stealing her otherwise warm features. I pumped my fingers, not giving her a moment to relax. But only because I knew this was the worst part. I repeated this until satisfied, pulling my fingers free. Ann immediately fell against the bed, her shoulders rising and falling with the deep, relieved breaths.
“Okay, you’re ready,” I informed her. And despite the circumstances, I was relieved to hear a sardonically dry chuckle escape her.
“Am I now?” I could only imagine what she must be thinking after being pushed so far to her limits. Especially when we’d hardly even begun. Sighing, Ann just rolled on her side, cautious to avoid sitting directly on her rectum. “How do we…”
“Um, all fours?” I offered, doing my best not to smile. I must not have done a good enough job, because sure enough, I found a glare being sent my way. Blowing a strand of hair out of her face, she just shook her head, too far past embarrassed to even care about the submissive position. I guess after having her butt cheeks spread wide open, there isn’t much that can really affect her at this point. She reluctantly moved to assume the requested position.
Kneeling on the bed beside her, I quickly took a moment to just look at her, loving this angle.
Shoulder blades sticking out of her back, she tiredly propped herself on thin arms, the low curve of her back rising into a soft round bottom. Long legs kneeled against the bed, mature thighs slightly spread in preparation for the impending penetration. And cradled bellow, her perky breasts loomed under their own weight, dropping towards the bed with their capped nipples at their direct center. In way, it struck me just then how impossible this situation really was.
“James?” she asked, an embarrassed huff leaving her mouth. But I just smiled, running my hand down her back as I crawled to face her offered backside.
Completely bent over, the line of her sex was entirely visible, her mature lips spilling out of the line that eventually merged with her crack. Slightly open, I placed a hand on each cheek spreading her that much more.
“Lots of lube,” Ann requested, hanging her head while I felt her bottom. Nodding, my free hand moved to grab the stray bottle while my other pumped the straining length of my erection. After releasing four generous donations of lotion into my hand, I worked the cream over my organ.
Slicked up as best as I was able, I whipped my hand clean on the blanket before waddling closer to align myself at her offered backside. Feeling me settle so close, Ann just sighed, lowering her head to the bed and allowing her cheeks to fall apart. Settling my hand on her tail bone, I angled myself at the slightly darker patch of skin and leaned my hips to move forward.
“Relax,” I murmured, my tone gentle and soothing. With the blunt tip of my organ pressed against her guarded gate, I could already see the ring twitching and struggling to allow itself to open. Applying the smallest amount of pressure, the spongy tip of my head pressed flat against her. The ridged core at its center stubbornly refusing to bend against the possible orifice.
Ann breathed deep, her back expanding and contracting as she struggled to find a sense of peace. One hand settled on her flank, the other rubbed slowly circled around the small of her back. After a moment, I could feel her begin to do just that. And as soon I felt her sphincter ease enough of its tension, my hips moved forward, forcing her to body to fit around the thick girth of my erection.
I watched her finger sink into the soft maroon comforter that covered the length of the bed. Elbows locked, her head slowly sank towards the bed while her rear stayed pointed in position. She grunted, deep in her throat.
The ring of her anus snapped around the ridge of my dick, locking us in place. Now that I was inside, it was a much simpler matter of pushing forward- though I did so slowly. Slick with the lilac scented lotion, the smooth skin of my shaft glided in.
For me, it was incredible. The view alone was the thing of dreams. This was what I’d been wanting. Her wide hips and mature rear posed to accept me. The tight enclosure of her rectum stretching to fit.
Forcing myself half way inside of her wonderful figure, I finally gave us both a chance to rest. Feeling me stop, Ann’s shoulders dropped. A desperate breath released that I hadn’t even known she was holding. Blinking, I couldn’t help but remember my inexperience in the subject and worried if I was doing this wrong.
Ann was in pain. Head bowed into her folded forearms, I couldn’t see her expression. Though I had no doubt it was currently tight and clenched. Bless her heart, despite the obvious discomfort she did nothing to stop me. Biting the pillow the stifle her grunts and groans. And doing everything in her power to accommodate her husband’s strange new fascination.
Letting her get used to the new sensation, I tried to think back to my horrible night with Shego. Take clues from how she’d been able to enjoy it.
Suffice to say, it was difficult to get any kind of reading off the villainous. The entre night she’d been so different from how I knew her. From everything I’d ever known about her. A few things caught my attention, though nothing concreate. Shrugging my shoulders, I quickly decide it could hardly be more uncomfortable than this.
I leaned forward, bending at the waist until the pale surface of my chest rested against her back. Brushing the length of her hair out of the way, my warm breath sighed against her bare neck, earning a shutter for my effort.
“Push against me,” I told her, feeling a slight jump at the sudden sound of my voice. Cupping her ribs, the course skin of my hands rubbed back and forth eventually reaching her breast. My hands slipped between the soft cotton bedspread and her softer skin, searching for each of her flushed tips to give them a squeeze.
She hadn’t been expecting me to talk. I could tell by the way her head turned to peek at me out the corner of her eye. “W-What?” so focused on the discomfort of something entering her rear hole, it took her a second to hear what I’d said. Kneading the softness of her boobs, my lips once again brushed the delicate warmth of her neck before answering.
“Push against me,” I repeated myself, my tone bleeding pleasure. While also the truth, I wanted her to hear what she was doing to me. How much I was enjoying the tightness surrounding me. “It should help. Make things easier for you.” I listened to the quick, sharp breaths squeezing against my chest. “Trust me…”
It didn’t happen right away. No doubt she was more than a little caution concerning that part of her body. But continuing to work her breast and leaving long lingering kisses against her back and shoulders, I could feel the tightness around me change, shifting. Loosing none of its tightness, the resistance that had been fighting me seemed to lessen a great deal.
I wasn’t the only one who could feel the difference. Right away I could hear her sigh in relief, as little as it might have been. I could actually feel her the tightness in her back relax.
“That’s my girl,” I encouraged. And I couldn’t believe how good it felt to say. Because it was true. It didn’t matter if she was already married to another man. It didn’t even matter if she thought I was another person. Right here, right now, she was mine. Mine to love, mine to touch, and mine to have.
Her breathing evened out. It was already markedly easier to slip the rest of myself inside, and I took this as my cue to continue. Keeping my position, my hips pushed forward stealing another inch. And at the same time, I released her breast to caress the soft skin of her belly. Continuing in this direction, the tips of my fingers brushed the wispy hairs above her crotch before finally reaching to feel the soft skin of her folds split apart for my fingers.
Ann’s breath stopped, a startled hand reaching back to touch my thigh. For the first time that night, Ann seemed unsure, a silent and immediate request for me to stop. With a knowing smile, I regretfully could not acquiesce.
For Ann, this wasn’t about her pleasure. But mine. And while I loved her for the sacrifice she seemed intent on delivering, I wanted more than for her to simply silent bear with a quick romp in her rump. I wanted her to enjoy it. Even if she didn’t expect to.
“James!” she gasped, head turned to the side so her voice was clear. There was fear in her tone, though not for the reasons one might expect.
Slowly pushing the last of my erection into her tight ring, my hand slowly drew through her long folds the way I knew she enjoyed. The mixing of sensations was startling, even more alien than just her first brush with anal. Pleasure mingled with pain, and she wasn’t sure how to handle it. I shushed her gently, earning another gasp. And just as my fingers pressed against her soft opening, our hips met.
“Don’t worry,” I told her, hearing the strangled sounds echoing in her chest. Moving in and out, two of my fingers teased the smooth walls inside of her, slow but insistent. Despite the strain of what was happening, her sex was still very much alive. A growing heat and slick liquid dipping down my palm.
“James!” she repeated, calling the name of the man whom she believed to be loving. Moving my hips, the long length of my erection pulled back, stopping just before half of it was free. Reaching with my thumb, I pressed its flat edge against her clit and forced myself back inside all the way to my hilt.
“That’s my girl,” I repeated, relishing in the moment. The effect was immediate, and I felt her already strained rectum tighten around me. I gasped right along with her.
“James! Stop, don’t- it feels…” she stopped, her voice betraying her own intent. This was new, interesting, and something she had been excited to experience. Even if she could never say it out loud. But it seems she never thought she’d be able to enjoy it. Nothing pleased me more than shattering that belief, and I took my time working my hand through her sex. Thighs quivering, she shook her head, grunting as pulled myself free a second time.
As much as I wanted to pound away at her backside, it was more fun taking my time. At a building pace, I worked my shaft in and out of her backside feeling the tightness around me adjust enough that I didn’t need to feel afraid.
It was just as good as I’d imagined. Even more than the delightful friction, even more than the beautiful woman underneath me, it gave me power. Something I’d lived my entire life without. It was like a drug coursing through my veins, sweet even as it burned away everything that I was. In a way, it was even better than the pleasure arching up my spine and pooling in the sack swinging between my legs.
This is what I’d been craving all this time. I thought back at the afternoons spent trying to relive myself with my hand, and I can finally understand the hollow sense of loss that seemed to always follow. It’s no wonder it couldn’t satisfy this urge. Only one thing could.
“Don’t be afraid” I muttered into her shoulder, my breath hot and heavy as it broke against the pale slate of skin. Daring myself to pick up my pace, I offset any pain my sudden urgency might cause by paying special attention to the warm bundle of nerves at the apex of her slit. “Don’t be afraid to feel good.” I could feel her, even now, trying to resist the motions of my fingers. But it wouldn’t last. Nothing could be denied forever
“James?” she seemed confused, maybe even a little frightened. It’s a wonder why. I could only imagine how different I must seem compared to the laid back, easy going Mr. Possible. But James wasn’t here, no matter how much Ann might think differently. And I trusted the mask to displace any suspicion.
My attention to her sex seemed to do its trick, and I smiled at the sound of her begrudged moan.
“Just let yourself go,” I continued, coaxing and gentle in the way my fingers seemed to seek out her weakest zones. In some way, I couldn’t believe what I was saying. It was like I was drunk, though on what I couldn’t think to say. But she continued to lay there and breathe for a number of moments.
With each pass of my hips I could feel her tighten around my length as well as my fingers. I prompted her for more.
“Mmm!” her voice cried. One of pleasure. She stopped, her voice shaking with the pace of my hips meeting her own. A small admission, but one that brought me the largest of smiles.
At the same moment, my hips pressed against the soft firmness of her cheeks, spearing deep into the back of her bowels. Her back tenses and she gasped. But around my fingers I could feel a newfound wetness dripple onto the mattress. Unable to speak, she just shook her head as if attempting to deny the proof flooding out of her.
What would James say if he saw the mother of his children behaving so voracious? I couldn’t help but wonder. Would she think about this the next time she was with him? Would she think about me? My already hard erection throbbed.
She was a mess by this point, in more ways than one. The familiar contraction of her sex was mirrored by her backside, and I knew the signs well enough to know she was on the edge. With this in mind, I finally allowed the speed of my hips to increase, a quick and deep penetration that sent ripples through the smooth and pale surface of her cheeks.
She mewled, the signals in her brain finally crossed enough to enjoy the treatment. Whither she actually enjoyed the sensation of me filling her backside, I couldn’t say. But she was far enough to simply sit back and enjoy the sensation of being filed.
Pulling back enough to stare at the back of her head, I watched her body jerk and shake from the impact of our bodies. Turning her head, her neck craned over her shoulder to look at me, blue eyes shimmering in confusion and lust.
“don’t be afraid,” I managed over the heaviness of my breathing, “and just,” my hips surged forward, “let,” my finger’s curled upward, “yourself,” and just like that I could feel the last of her resistance melt away. The tightening muscles around my fingers redoubling in their effort in a splash of liquid arousal.
“Feel it.”
I came with a relishing smile, electricity singing through my body from the top of my head all the way to my toes. Warmth, pleasure, everything I ever was surging up and out my body and into Ann’s. And all with the knowledge that I’d been able to bring her over the edge with me.
Warmth flowing into her bowels, Ann’s body naturally tightened around me. The tight ring of muscles fighting to stop the strange inflow of substance that was normally turned to the opposite direction. With her hand, despite the discomfort, she made the effort to reach back and hold my hip, gentle squeezes coaxing me through a mind bowing orgasm. All the while with her own release crushing my fingers with its strength.
Breath held, when everything was over the room was filled without collective gasps of pleasure. I nearly fell on top of her. A shaking arm braces against the soft cushions below us.
Ann didn’t say anything while I caught my breath. I could feel the warmth and sweat drip off of me into her pale back, mixing with her own exertion.
For a single, wonderful moment, I even forgot about what was waiting for me at the end of the day. That I’d never see this wonderful woman again. That I’d never get to feel her soft skin, her warmth, her love. And when that moment ended, I found my heart breaking all over again. Both for the loss I was feeling, but now, even more that I understood what I was losing. For the first time, I understood what I wanted. Why I’ve been so driven and lost since I’d started collecting this little treasure trove of magic and technology.
Control. Over my life. Over myself. Just to have it, the one thing that I never seemed to be able to obtain growing up. And now Yori was coming to take me away, as well as any choice I might have had. Unfortunately, understanding why I’ve been so upset didn’t answer the question of if I could go through with it.
”James…?”
Hesitant, Ann’s voice called out in a muted tone. I jerked, looking up in surprise to find myself still inside of her. Though considerably softer. Realizing that I must have drifted off without meaning to. I slowly eased my hips back, earning a deep sigh from Ann when I finally pulled free.
“!” I stared down at where I’d just been inside of her and eyed the afflicted area. Flushed a brighter color, the small opening remained slightly stretched from our activity. Other than looking a little irritated, I couldn’t see anything that would leave any permanent damage. I didn’t get long to look because soon after feeling her back passage empty, the older woman’s position proved to be too much - forcing her to slowly fall to her side.
“How are you feeling?”
Curled up in on herself, her face was pinched. Against her, I pressed my front to her back and propped my head up so I could look at her. In response to my question, she just shook her head, a wry smile fighting through the tight expression.
“Very similar to a colonoscopy patient, I imagine.” Turning her head, her eyes searched for mine. She reached up for short, warm kiss. “And… maybe a little surprised?” she asked. I immediately pressed our naked, sweaty bodies close together in a tight embrace. I kissed the back of her head
“You were incredible.” I promised. And that was an understatement if anything.
Ann smiled, despite herself. Turning around, I loosened my hold enough for her to press her face into my chest. For a second she held like this, just breathing in the heavy scent of our two bodies. When she finally broke away, the tension in her face was all but gone. Though I knew it would be a good few hours before she would be sitting without at least some difficulty.
“Did you enjoy it?” A bold question, but one I needed her to answer. After all, I doubted Ann expected to anything so crass in her life time. Not if her reaction to my request was anything to go by. So to suddenly find herself completely undone by the action, she was no doubt a bit shaken.
Ann didn’t answer right away, a quire look in her face as she recalled what had just happened. For a moment the tight line of her lips made me worry, but it slowly curled up into a half smirk. “I… Yes.” She admitted, her voice quite. Almost shamed. Her hand wormed up to pressed against my stomach. “Though, I’m not sure how I feel about that if I’m being honest.” Her features stayed worried, a frown on her lips. I took this in with a steady calmness before reaching for her face.
I turned her toward me, eyes connecting in a way that she could see the honesty of my next words. “If you liked it, than that’s all that mattered. No one, or thing can take that away from you, and there’s no reason to feel ashamed.” Her cheeks took on a light color, and she seemed to melt a bit against me. I took this as a sign of comfort before welcoming her into my arms once again.
When she looked back at me she held a brilliant smile. I couldn’t stop from reaching down to plant another lingering, searing kiss. When I finally pulled away she was chuckling, deep and in the back of her throat.
“I must say, I wasn’t expecting you to get so…” she paused, seeming to look for the right word. “Naughty.” It came out hushed, like she felt odd even saying it. But watching her dissolve into another fit of giggles eased any worries I might have had. “I suppose there’s nothing wrong with enjoying something a little strange.” her eyes turned soft. “Thank you, dear.”
“So I didn’t scare you?” I’d been worried about that. It wasn’t everyday a husband comes home suddenly asking for things like anal. Pulling away from me, Ann’s smile was soft and lazy. She shook her head.
“Of course not. Startling, yes. But I think with some time to heal,” she hesitated, like she needed to double check that she was in fact okay with what she was saying, “and a bit of wine, I think I wouldn’t mind trying again some time.” She rubbed her thighs together, the sated wetness still seeping out of her. “I can’t say it was all bad after all.” And turning to look at me, when her brilliant smile flashed I found myself unable to join her. The word, “again,” echoing until it was all I could hear.
I didn’t saying anything for some time, lost in thought. Outwardly I took that time to enjoy her naked figure stretched out on bed next to me. When I finally did find it in me to answer, my voice was calm. Subdued. Whatever uncertainty I had been feeling in the past gone.
“You look tired.” I murmured softly in her ear. Lids already half drawn, she could only agree with me.
“Guess this cold is still draining me,” she closed her eyes and laid back against the bed.
“That or the three orgasms,” she gave a small laugh.
Her hand reached out caress my shoulder. “Any chance you’d want to skip the rest of work and sleep for a bit?” Her tone was light, but not hopeful. Considering James’ love for his work she no doubt figured it wasn’t very likely. She had no idea how much I wanted to say yes. But unfortunately, Kim was still waiting for me. And I couldn’t decide on anything without seeing her first. I knew that now.
“I’ll stay until you fall asleep,” I answered. And this was enough to earn another smile. “Here, let me grab a blanket.” One that wasn’t soaked. And again, she nodded, moving her hand to let me slink off the slide of the bed.
At the foot of their bed a thin, knitted, red blanket was folded. Opening it up, I happily draped it over her naked body taking special care to get a few more glances of her pale complexion. Feeling the spun fabric fall over her, she smiled at the added warmth and pulled it under her chin. I joined her, laying myself on top of the layer after only a small detour.
“I love you,” I promised. And god was it true. Running my hands up and down her arm, she smiled, but otherwise didn’t respond. Eyes closed and on her side, she seemed to be even more tired than I’d already guessed. And was already slipping away.
Taking these last few moments for myself, I watched her eye lids flutter shut and breathing even to a slow deep crest. And only when I was sure that she’d was fully unconscious, did I reveal the long metal cylinder I’d hidden behind my back and fired its purple beam directly into her back.
A quick flash was the only evidence I’d done anything at all. Open mouthed, she continued to sleep without a care, and the only difference being it would be another eight hours before she was awake. I leaned down to kiss her temple before standing to dress in my discarded clothes.
Staring at the object in my hands, I knew it wasn’t how I wanted to end our time together, but I had other matters to attend to. What I should have done from the very beginning.
Next chapter – March 19 – What she needs from me: After his time with Ann, Ron finds himself with a better understanding of his past actions and motivations. confronting Kim after so long, has his decision to leave been shaken? Or is this really good bye for the both of them? Either way, answers will finally come to light after being hidden for so long.
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- 11
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Ron's toys