Cookies & Toys

It had been a few weeks since I dared to delve into the depths of my derriere, and it was all I could think about. I knew I needed to set aside some time to indulge in this guilty pleasure once more. The anticipation was almost unbearable. The thought of experiencing that euphoric release again was enough to make me shiver. Within a week, stroking and fingering my rear had become a normal part of my masturbatory routine. Reigniting my desires as my typical self-pleasuring had become mundane and boring. And don’t get me started on my sex life, which was as barren as the Saharan.

My fingers were working overtime to fill the extra hole, and while they met my expectations, I needed more. This growing desire drove me to the internet to figure out my next steps, as I didn't want to go into it blind. I'd heard and read horror stories, and I didn't want them to be my reality. I was anal when conducting my research. The key takeaways: proper hygiene, plenty of lube, a gradual increase in size, and adding more lube! With this newfound knowledge, I wanted to buy toys or a training set, but there were far too many options.

When faced with too many choices and analysis paralysis, I consult my friend Mia. She assisted me in purchasing various items, such as clothing, makeup, and my bong, in the past. She even helped me pick my first vibrator, so I knew she'd be willing to help me choose a training kit. Was I too reliant? Maybe, but I valued her opinion. I texted Mia to see if she was free this weekend. She enthusiastically texted back, inviting me over Saturday afternoon. Eager to catch up.

The day arrived, and for whatever reason, I was a little nervous to ask for Mia’s thoughts on buying an anal training kit. Her and I’ve shared intimate details about our lives before and knew we could confide in one another. But I guess it’s always a little terrifying to reveal such personal and vulnerable details. Even if that someone is your best friend. Lost in thought, I didn’t realize I had walked up the two flights of stairs and was standing in front of her navy-blue door. Taking a deep breath, I knocked on her door and waited with an anxious heart for her to answer. I heard her unlock the latch, and as she swung the door open, I greeted her with a warm smile.

"Lilith!" Mia leaped forward, putting her arms around me and drawing me in.

I laughed and reciprocated her hug before closing the door behind me. "Hey, how've you been?" I asked before releasing our hug.

"It's baking day, so I can't complain." She smiled and tickled my sides, and I wiggled away from her touch, laughing.

"I can't wait to see what delicious treats you've whipped up this time," I said, following her into the kitchen.

Her home was dim, with blackout curtains drawn and unscented candles lighting the room. Mia's signature chocolate chip cookies wafted by my nose. My mouth began to water at the thought of munching on her chewy cookies—an orgasmic experience in and of itself. I sat at her kitchen counter and watched the microwave timer count down, indicating when the baked goods would be ready. During that time, we caught up on work, upcoming social events, and any juicy rumors we had heard. The alarm went off. Mia took out the golden, steaming chocolate chip cookies, placing them on a rack within arm's reach of me. Tempting me. She turned away from me, the opportunity presenting itself. As I reached for the goodies, the silence broke with a loud thwack! Mia's spatula caused a stinging pain in my hand.

"Fuck, Mia, that hurt!" I rubbed the back of my hand to relieve the pain as I glared at her.

With a sinister smile, "You have to wait for them to cool off," she stated with a stern yet playful tone. She was always in favor of corporal punishment.

"Fine," I pouted before standing up and approaching her refrigerator.

The fridge was cluttered with bills, photos, and menus, all held in place by magnetic letters. Some of which spelled the words dick and pussy. Mia's deprived sense of humor matched mine, which contributed to our strong bond. I opened the fridge and searched through the contents for her milk. With the milk in my hand, I closed the door and turned around to see her eating a cookie. I felt betrayed.

 "The audacity!" I huffed.

She licked the chocolate off her lips. "I had to test one to see if they were poisoned," she giggled, believing she was clever.

I slammed the milk on the counter, causing the liquid to slosh around. "You made them!" I said in a playful tone as I nudged her out of the way to grab a cookie for myself.

That first bite was so gooey and warm. Chocolate chunks bombarding my tongue made me moan with delight. Mia looked at me, intrigued, but she knew I made such noises when I ate something I enjoyed. She turned around and chuckled as she poured us both glasses of milk. Nervous but full of sugary confidence, I decided now was the best time.

"Hey, can I ask you something rather personal?" I paused for a moment as she handed me a glass. "And intimate?"

She smiled and cocked her head in curiosity. "Of course. Grab another cookie, and let's relax on the sofa." She grabbed another cookie and led us into her living room.

Her couch was more of a loveseat that rested against the wall. In low light, it could be mistaken for black, but it was actually a deep purple. A rustic coffee table was nearby, cluttered with magazines, burned candles, and a potted plant, with enough room for our drinks. The entertainment center across from us matched the coffee table in appearance. The TV sat in the center with two other potted plants flanking it. She disliked the fact that the walls were white. The landlord was strict about which colors were acceptable. Mia despised the choices. The wall behind the couch was covered in a huge black-and-white mandala tapestry. It gently waved whenever the air conditioner or heater kicked on. Mia's apartment was cozy. We burrowed into the armrests of the couch opposite each other. She looked at me expectantly as I worked up the courage to continue my line of questioning. The room was filled with silent anticipation.

She slid her barefoot across and bumped my thigh. “So, what did you want to ask?”

I turned to face her and looked into her brown eyes. “Have you ever done anal before?” I could feel my face igniting from asking the question.

Her interested expression turned into a blushing smile. "That certainly is an intimate question." She leaned in closer. "Why do you ask?"

I took a deep breath and explained how my interest developed over time. How I'd fixate on the appearance, seek out porn and erotica depicting such acts. How, in a euphoric state, I took the plunge a few weeks ago. And have since incorporated it into my regular self-pleasuring routine. She listened intently and, to my surprise, admitted to engaging in the act herself on a regular basis. Both sex and masturbation. She calmed my nerves as we talked, and I asked for her advice on purchasing a training kit.

"Don't waste your money, honey!" Mia spoke while tapping my thigh. "Follow me." She hopped off the couch and went into her bedroom.

Curious, I set down my empty glass of milk on the coffee table and followed her into the room. Mia's room was filled with warm light from lamps flanking either side of her queen-sized bed, unmade with purple blankets bundled on top. I heard her rummage through her closet and looked to my right to see her bent over with her butt sticking out. Her shorts left little to the imagination. My brow raised, my lips curled—a chance for revenge presented itself. As I stepped forward, the floor creaked beneath me. My hand poised for a surprise meeting with her voluptuous cheeks.

"Don't even think about it, Lily." Her words were muffled in her closet.

"I don't even know what you're talking about." I gave a halfhearted chuckle and abandoned my revenge plot.

Mia huffed as she lifted something from the closet. Turning around with a black leather chest nestled in her arms. The betraying floor creaked again as she walked over and placed the chest on her bed. I followed behind her, taking in the simple details of the chest. All black, with two golden latches that prevent the lid from opening freely. She looked over her shoulder with a sly smile before flipping the latches open with an audible clack. She lifted the lid as I looked over to see a collection of sex toys cradled in a velvet-burgundy interior.

My wandering eyes admired the variety of toys in the case. Dildos, vibrators, plugs, clamps, and other accessories contained within. Her collection captivated me. I was aware she had toys, but I had no idea how extensive her arsenal was until now. The sounds of her rummaging through her stash, choosing and removing toys from within, broke my spell. I could feel butterflies in my stomach fluttering down to my loins, rousing my pussy.

I stood next to her, my eyes wide with surprise, while hers were full of lusty pride. "You're a kinky girl," I giggled.

Mia reached down and grabbed the first toy, then handed it to me. The pink plastic was smooth and soft as my fingers ran along the short, tapered shaft. It ended in a stem that connected to a flared, t-handled base.

"This is a good starting plug, as it's a little bigger than your pinky finger," she explained. "With comfort, it'll stretch you and train your little hole. Perfect for all day use with its softness and flexibility."

My pussy began to dampen at the thought of wearing the plug all day while my asshole yearned for it. She snatched the toy from my grasp and replaced it with another. The metal shone and reflected my captivated expression. It was also tapered, but wider and heavier in the hand. The flared base was rounded and encrusted with a clear jewel.

"Now, that plug is a little bigger, about the size of two of your fingers stacked over one another." She demonstrated using her own fingers. "Once you get used to the little plug and can insert it and take it out with ease, you can move up to that one." She took the metal plug out of my hand. "You can wear this all day too, but I suggest starting at 30 minutes since it's heavier; it'll tire your little booty out faster," she teased.

I clung to every word she said and could feel my pussy leaking with excitement. She returned the metal plug to the bed and picked up the two remaining toys from her private stash. She extended her left hand and presented me with a string of beads. The beads grew in size as you moved down the rope, eventually ending in a large loop.

"These are anal beads." Her smile was warm. "Insert to your level of comfort; the end goal is being able to insert all the beads." The last bead was approximately the size of the metal plug. "And, when you're right on the edge of your orgasm, pull on the loop and enjoy the ride." She gave me a playful wink before placing the beads on the bed.

"Last but not least," she smiled deviously as she presented the last toy in her possession. "The piece de résistance, the dildo." She spoke with a ridiculous French accent, and I couldn't help but laugh.

Snickering, she slapped the dildo against the headboard of her bed and removed her hand. She flicked it with her palm, making it wobble up and down. The tip captured my attention. It appeared fleshy, slender, and roughly the size of an average cock. The thought of the dildo deep within me sent shivers down my aching pussy and eager ass.

"Once you've mastered the metal plug, you can start working on the dildo." Her voice rose with excitement. She took a deep breath and looked me in the eye. "And these are now all yours."

"Really?" I asked, unable to contain my excitement.

Mia nodded and told me that she no longer used these toys and was considering throwing them away. Yet, due to my newfound interest, she offered them to me instead. I was ecstatic and couldn't wait to get home and play with my new toys. My fingers were tracing the smallest plug on the bed, deciding when I should start this journey. My heart was racing, my panties were damp, and I was absorbed in the possibilities. Her kindness and generosity warmed my heart, but the unexpected slap to the ass took me by surprise. I yelped and moaned, feeling both pain and pleasure, and brought my attention back to her.

"Now, drop your jeans and panties and bend over the bed," she said with a sly look.

Surprised by her sudden command, I could feel my face turning paler than it already was. Then I felt my cheeks flush with embarrassment and excitement at the prospect of doing what she had said. My arousal was the most intense emotion I experienced. My pussy soaked my panties in her juices; I was practically swimming in my fluids. Mia knew me very well. We've never gotten intimate together. Except for kissing when we're drunk, we've seen each other naked several times too. But this was different. She was aware that when I was horny, I became a little submissive slut who required a gentle nudge to comply.

"Be a good girl. Drop'em and spread'em." She walked over to her dresser and started digging through the top drawer.

My hands were shaking, but I took a deep breath to regain my composure. My fingers unbuckled my black studded belt and lifted the button that held my gray skinny jeans together. Lowering the zipper, I tucked my thumbs under the waistbands of both my garments and wiggled my way free. My pants and panties were down around my ankles, and I bent over her bed, my face resting on her mattress. My eyes shifted to the toys she had given me, and my head was filled with anticipation.

"I forgot how cute your bubble butt is." Her voice was playful, and I could hear her approaching me. A single finger of hers pressed against my right cheek. "And the adorable little mole you have." I could feel goosebumps spreading across my body.

I could hear her kneel behind me. With her so close, I'm sure she could taste me from the scent emanating from my gooey pussy. I let out a soft moan as my hips bucked from her finger gliding up and down my slit.

"A little excited to be plugged, huh?" Mia's sticky finger slid up to my asshole, rubbing my juices all over.

I sighed in agreement, lost in the sensation of having someone else play with my rear for the first time. I heard the snap of a cap being opened. "Spread your cheeks for me, Lily." Her tone was gentle yet stern.

Without hesitation, I reached back. My black, chipped, nail-polished fingers gripped and spread my cheeks for her. I soon felt liquid drop onto my small hole, followed by her wandering finger coating the ridges. She pressed the pad of her finger against me and slid her digit inside. Her gentle probing radiated a mix of pain and pleasure as little moans escaped my lungs with each thrust. She withdrew her finger and grabbed the pink plug next to my face before disappearing from view. Seconds passed, but it felt like an eternity before I felt the plug pressing against my eager hole. I held my breath while she pressed the plug against me.

She put a hand over mine. "Relax and breathe, Lily." Her voice was soft, reminding me to let go.

As I exhaled, she pushed the plug further in. I groaned, my body resisting the toy. I gave in and swallowed the plug until it was firmly between my cheeks. A pleasurable pulse echoed throughout my body, with my ass being the epicenter . My grip on my cheeks loosened, obscuring the plug between them. I closed my eyes to concentrate on this new sensation. Something other than my fingers was inside of me.

"Your ass is made for anal." Mia broke the trance I was in. "You took that plug with little issue." Her hand stroked my bare bottom. "I'll also give you a bottle of lube I keep on hand." She opened the black chest again, reached inside, and took out a new bottle of lube, placing it next to my toys.

I was barely listening to her words as the desire to fuck myself grew stronger by the second. But both of us heard the front door open and close. Lifting my head from her bed and looking up at Mia, her gaze met mine.

"Shit, I thought he was going to be at work all day," Mia sighed as she retrieved a small backpack from her closet and placed it next to the bed. "Fix yourself up and store your things in here. I'll keep him distracted." She smiled and tapped my bare bottom before walking out the bedroom door to greet her boyfriend, Liam.

I could hear the two talking, but I couldn't understand much because I was in a hurry. My fingers gripped the waistband of my black panties, pulling them up along my legs to cover my needy pussy. My jeans were quick to follow: buttoned, zippered, and studded belt fastened. I took the backpack and began putting my toys in it. Metal plug: check. Anal beads: check. Dildo? Still bobbing on the headboard. I grabbed it by the shaft and pulled, but the prick remained stubborn. I squeezed the base of the dildo, and it came off with ease. I threw it into the bag. Bottle of lube: check . Okay, where is the pink plug? My eyes scanned the bed as panic set in, but then I felt a small pulse reminding me where it was. I smiled, feeling a little naughty.

I walked over to Mia's opulent dresser and looked into the mirror above. I adjusted my hair and took a few deep breaths to calm myself. I walked out of the bedroom, feeling confident enough to hide my aroused demeanor. I saw Liam and Mia talking and laughing. They both smiled at me. Mia's grin was more devious, whereas Liam's was friendly and innocent.

"Hey, Lilith," Liam said, waving a cookie in his hand. "How've you been?" he asked before taking another bite.

The kitchen counter stood between us as I approached them. "I'm doing good," I said while leaning over to grab another cookie for myself. "I wanted to get some Mia and me time." I gave her a playful wink before biting into the cookie. "Alright, Mia." My feet carried me to the front door. "I should get going," I sighed with a false sense of exhaustion.

Mia smiled, knowing what my true intentions were, as she followed behind and opened the door.

"Bye, Liam!" My fingers waved as he nodded, caught in the middle of a bite.

"Enjoy the rest of your day," Mia purred before slapping my ass one final time. I jumped out of her doorway and muffled the sounds of pleasure produced by her hand. She closed the door behind me, allowing me to breathe.

With the bag slung over my shoulders, my legs began to descend the stairwell. With each step, the plug pulsed inside me. Reminding me of its presence. My feet were on autopilot, and my mind was in a blissful haze. The chime from my car jolted me out of my trance. I shifted into reverse and began my five-minute drive home.

As I turned right out of the apartment complex, the divot between the street and sidewalk jostled my car. What would've been a normal bump echoed through the plug. I became acutely aware of every bounce, crack, and dent in the road. I was desperate to return home. Again, on autopilot, I don't recall the drive, but I was parked outside my apartment complex. Only one flight of stairs and my door separated me from the orgasm that was raging inside me.

My hands trembled as I turned the key to unlock my front door. The metal in my hand shook. I fumbled to turn the lock; it took everything in me not to break down the door and tear my clothes off. With the door open, I slammed it shut and tossed the bag to the floor. I unbuckled my studded belt and unfastened the button on my jeans. I dashed to my couch, pulling my jeans and soaking panties down around my thighs. In pure desperation, I tossed myself over the armrest, exposing my ass. My fingers needed no guidance; they found my sensitive nub and rubbed with fervor. With my other hand, I pushed the plug in, filling me up even further.

Moaning and crying into the fabric of my couch, I felt my orgasm rip through me with vengeance. For being denied for so long. Wave after wave crashed into me, knocking the wind out of me. I had no idea how long the orgasm lasted; it felt like I had come for hours. My muscles were still aching from the tension. I craved more.

Satisfied for the moment, I stood up from the couch armrest, grabbed the hem of my hoodie, and pulled up. I tossed my hoodie on the couch and reached behind to unclasp my black bra, shrugging off the straps. I let it fall to the ground, and I felt the cold air harden my nipples. With my pants still down around my knees, I bent down to untie the laces of my sneakers, kicking them off along with my socks and jeans.

Naked and free, I entered my bedroom and turned on the lights, hoping to see the plug between my cheeks in the mirror. I stood in front of the standing mirror flanking my dresser, admiring my flushed body, brimming with excitement. I turned around and peeked over my shoulder, spreading one cheek with my hand. There it was, the small pink plug staring at me. Simple and beautiful, I wondered what the metal plug would look like inside my body, but that was for another day. My pussy was begging for attention again.

I lay down on my bed, my bare back against the cool sheets. I spread my legs and slid a finger down to my clit. My other hand grabbed one of my breasts, and my fingers rolled over the nipple. As I became immersed in the sensations, I let out a gentle sigh of satisfaction. Even when I wasn't playing with the plug, it throbbed a gentle, reminding rhythm. I imagined various scenes and scenarios involving me getting fucked in the ass. My ultimate goal is to get a real cock in my ass. But I knew I had to work up to such activities.

The gentle touch of my hand between my legs roughened, and I rubbed my clit harder. The fantasy intensified: a faceless man with his hands on my hips, slamming his thick cock into me, stretching me. Making me his. My legs clasped together, bucking wildly, as an orgasm pulsed through my core. My ragged moans echoed around the room. I could feel the plug wriggling in and out of me with each contraction.

My chest heaved as I tried to catch my breath, and my pussy became sore. My hand slipped away, trailing up my abdomen before resting on my breast. My skin was sticky with sweat, and a layer of perspiration covered my naked body. My eyes still closed, I reached down and removed the plug from my satisfied tush. I rolled onto my stomach and threw my blanket over me. As my breathing settled, I started to drift off. The last thing on my mind was how much I wanted to have a plug inside me every day.