"How's my good boy doing today?" I could hardly look up from my cereal in time to receive Alice's wet kiss on my cheek. "All ready for your big day?"
I smiled in spite of myself at the older woman's affectionate greeting. In the weeks since our first fuck, Alice had fully embraced the paternalistic side of herself that had only been teased up to that point. The head pats and 'good boy's had just been the tip of the iceberg, apparently. She was a woman transformed now, entirely absorbed in her self-appointed need to take care of me. I wasn't complaining; the tall, busty goth goddess who'd moved into my spare room a few months earlier was gorgeous company.
"I think so. I hope so. No, I am. I'm ready."
"Awh, come on now," she said with a grin. I couldn't decide if her black lipstick made it more genuine or if I was just in love. "Just remember what we practiced and you'll be fine."
"I know. I do. It's just..."
"Out with it, baby boy," she said, reaching into the cabinet for a bowl before coming to join me for breakfast. The generous view of her thick, firm ass nearly made me whimper.
"I really want this job. I'm worried I'll fuck it up."
The look she gave me while pouring her cereal told me how ridiculous I was being. "Well," she said, "I'm certain that you won't, but even if things go wrong, I'll still be proud of you either way."
Proud of me. Not something I heard much of growing up, the words set my heart racing coming from Alice. Roommate or not, her approval had become tremendously important to me in the time we'd spent together. It might have had something to do with how often she drained my balls, my latent mommy complex, or some Freudian mix of the two, but hearing her say things like that always got me going in ways that they shouldn't have.
"Thanks," I replied. "I do need to get going though. Wish me luck?"
She shook her dark shock of black hair vigorously in refusal. "No sir, I will do no such thing. You don't need it." She laughed at my pout, "Get home quick and you can be lucky all afternoon if you want."
*******
True to her nature, Alice was right; I didn't need the luck. One firm handshake, and a few signatures on some HR forms later, and I was back in my car to race home with the good news.
This was it. The job was a good one, but the occasion to give the elder emo woman something to be proud of me for was so much more than just that. This was going to be my way in.
Into her ass.
I fought to control my breathing as I rehearsed my speech on the ride home, but my sweaty palms and the lump in my throat made it hard to focus on the job at hand. I'd run this through in my head a hundred times, a thousand, but I never felt ready enough to broach the topic of what I had come to desire more than anything on God's green earth.
Alice's asshole.
I don't know where it came from, or what part of our dynamic had given birth to it, but I had become wholly obsessed with the only thing she hadn't given to me. Please understand, this wasn't some craving born of idle curiosity; it was a need. I needed her ass. All day and night, I was consumed painfully by my need to touch, feel, and fuck her ass.
I'd had her in every other way imaginable. Casual handjobs while we watched esoteric indie horror films on the couch, morning blowjobs in lieu of breakfast on Sunday mornings, sweaty, breathless creampies on any surface or piece of furniture that would bear our weight. And the abuse she put my face through! Our first encounter should have made it obvious enough, but the woman loved nothing more than to plant her greedy pussy on my face and grind herself against me for hours on end. I wasn't even sure I had taste buds left anymore. Even her frigid little toes had worn my cum after one particularly confusing new experience.
But it wasn't enough. Not compared to my final prize.
The elevator ride up to our shared apartment was torturous, and I was worried I might vomit from the nerves. Still, it had to be done. While her wardrobe of black outfits covered a dazzling spectrum of complexity and variance, Alice spent most of her time at home in nothing but baggy t-shirts; if I was forced to come home to find her sleeping on the couch with her bare ass peeking out from under the hem of a shirt one more time, I might explode.
The elevator dinged, and my mouth watered like Pavlov's hound. It was an effort not to vomit at my own door. Now or never.
Frustratingly, it was never. Well, not just then at least.
A note on the counter read "Sorry kiddo, I got called in for an early shift - the barback they scheduled didn't show up. Tell me how the interview went when I get home? I'm excited to hear all about it! xx - A."
I nearly screamed in frustration.
I needed an outlet. Something. Anything to take my mind off of what I had convinced myself I'd be having at that moment. In hindsight, I was definitely thinking with my dick, but the solution that presented itself to me right then seemed perfectly rational.
I'd go into her room.
I hurriedly shrugged out of my work clothes and into something more comfortable; some loose shorts and a dirty tee. The minutes leading up to what I was about to do felt so right, like the solution to all my problems lay clearly before me. A serene calm overtook me and I decided to christen the occasion with a beer from the fridge. A Tupperware with another cute note from Alice, telling me I was free to eat her leftovers, felt like all the blessing I needed, like she was right there saying "Go ahead, it's okay."
I'd never been into her room before. It had always felt like a line that I couldn't cross; if we weren't fucking on the sofa, it had always been in my room. I'd only ever caught glimpses into hers on a few occasions. It was time to change that.
I pushed through the unlocked door with trepidation. I wasn't sure what I'd expected to find, but was too exhilarated to be disappointed by how ordinary the space was. Larger than my room by a good bit, hers was entirely unremarkable in its simplicity. Given her patchwork tapestry of savage-looking tattoos, all-black aesthetic, and encyclopedic knowledge of Nordic death metal bands I'd never heard of, I expected...more. The bed, covered in a plain green duvet, was freshly made. A dresser stood along one wall next to a cluttered makeup vanity. Aside from a few scattered items of discarded clothing, there was nothing here to suggest that the woman I knew lived here at all.
I toed into the room cautiously, fighting a rising tide of realization that this was all a bit of an overreaction to not finding her home. This couldn't be it. I needed something, some pay-off for the risk that I'd taken in coming here, some small token to remind me that I was waiting for something truly special to come home and reveal itself to me.
The nightstand. It had to have something; every woman I'd ever known kept her toys in the top drawer, and Alice was certainly the kind of girl to entertain herself liberally when I wasn't around. I pulled the drawer open and was rewarded immediately.
Not one or two, but five toys laid against the cheap wood bottom amid a tangle of charging cords and knick-knacks. A trio of rubber cocks stared up at me in a neon array of colors that clashed heavily with Alice's carefully curated look, and something that I knew would somehow mimic the sucking sensation of human lips sat in a disorganized heap. Something else dominated my attention entirely though.
Shiny and silver, the heavy metal plug set with a gaudy, cheap-looking gemstone in the shape of a heart rolled against the front wall of the drawer with a heavy knock. I stared, mouth agape, for long seconds while I considered everything that the thing represented. It was a butt plug. It went in butts. Alice's butt, to be exact. If Alice had a butt plug, it meant that she put it in her butt, and if she put things like this in her butt then maybe, just maybe, she put other things in there as well.
The shamefully adolescent line of reasoning struck me dumb. I dared to reach out gingerly, plucking the cool metal thing out of the drawer and holding it up like a precious stone. It was...beautiful. The urge to pop the thing into my mouth, just for the sake of being closer to it, nearly overtook me. It didn't feel like enough just to know that the thing existed; I needed to possess it. I needed to make it mine. I needed it with me, near me, next to my bare skin at all times.
What I needed was to put it back and go relieve the unbelievable pressure in my shorts immediately.
*******
Though Alice returned later that night to celebrate my success with me, I'd simply beaten my poor, abused cock raw by the time she got home. I lied when she asked if I wanted a blowjob to celebrate and told her that I only wanted to lay back and let her grind herself silly on my face again for all the help she'd given me in preparing.
She was, obviously, more than happy to oblige, and I nearly rose to attention at the thought of how close her tight little asshole was to my eager tongue; one miscalculated bump of her hips and I'd be nestled deep in my prize. Still, I was truly worn out and wanted to be sure I was at my best when I made my move. Alice gleefully abused my face until my lungs screamed for mercy, as was her way, and left me in a giddy little heap with a slimy grin on my tired lips.
Days passed before I was even tempted to consider my proposal again. The high of discovering her plug had fueled me into a fit of punishing masturbation; I hardly had it in me to fuck her the next time she asked me to. Still, seeing her bent over the back of the couch as she asked for my cock in her sultry way was enough to get me going, not to mention the promise of an opportunity to spread her fat ass meat and get my eyes on her delicious-looking hole.
"Fuck, baby boy, you make Mama feel so good!" she moaned. The 'mommy' stuff only came out on rare occasions when she was feeling particularly needy. "Smack my ass! Come on baby, smack my ass harder!"
I railed her, cracking sharp smacks on her already bruised flesh while I pounded, knowing full well that anything less than my level best would be outright rejected by the Amazonian bent over in front of me. In the early days, I often spent my time behind her marveling at the rich inkwork that covered much of her broad back, watching the way that the inscribed insects and devils danced under my assault. No more though; all I ever cared about now was staring obsessively into the waiting void of her scrunchy pink asshole.
"Fuck mommy, come on baby boy, fuck mommy harder!" she screamed, turning as best she could to look back at me.
