A sexually inexperienced 19-year-old who works at a coffee shop after school. Christopher is shy and awkward, especially around attractive female customers.
Mistress M
Businesswoman by day and dominatrix by night. Mistress M has a leather and bondage fetish. She regularly meets other kinksters online or at BDSM clubs.
I knew I was going to make him my bitch from the first day I saw him. He was always so fucking polite.
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She was the best part of my day. Working at the coffee shop wasn’t exactly my dream job but it paid for gas in my car and nights out with friends. Most of our customers were stuffy businessmen and giggly teenage girls that ordered smoothies and chocolate chip cookies. But not her. She was different.
I knew I was going to make him my bitch from the first day I saw him. He was always so fucking polite.
“Hello, welcome to Fresh Grinds. Would you like to try our new salted caramel latte with extra foam and fresh ground beans?”
No, actually, I wouldn’t. The only thing I want grinding is my pussy against your face. Who did he think he was fooling with that innocent, coy smile? Sure, he was probably just legal by a few months (or weeks), but that’s exactly how I like them — young, verile, and eager to please.
I visited the same coffee shop every morning on my way to work. Specifically to see Christopher. In all honesty, their coffee sucked and so did their bran muffins. But every night when I left the office I found myself fantasizing about Christopher bent over my knee with a ball gag in his mouth. My favorite whip cracking against his tight, pale white ass.
But how would I get him there?
I mean, I consider myself a fairly attractive older woman. My large breasts are still perky and full. My athletic legs look killer in heels and my lips are soft and supple (thanks to monthly collagen injections). Some younger men like older women. The smart ones, anyway. The ones who realize that sexual beings like myself have plenty of experience. We know our way around a bedroom and a cock. I bet I could make Christopher cum without ever touching his virgin dick.
The thought of having him as my sex slave was too much bear. I needed to make it happen. Now.
The next day I entered the coffee shop just like I did every other morning. Except for today, I unbuttoned an extra button on my blouse and wore my favorite black leather push-up bra. The shiny material was slightly visible beneath the red silk shirt. My black pencil skirt was snug against my hips, accentuating every curve. I could feel my swollen pussy lips crammed together beneath the tight fabric.
My heels clicked across the coffee shop floor as I approached the counter. He was there — looking as young and delicious as ever. He smiled and greeted me as usual.
“Hello, welcome to Fresh Grinds. Would you like to try one of our freshly baked orange and cranberry scones?”
I found myself staring at his lips. His thin, moist lips. I wondered if he’d ever eaten pussy before. I quickly realized Christopher was still waiting for me to respond to his proposition for a scone and the line was growing behind me.
I brought myself back to reality and smiled.
“No coffee for me today, thanks.” I slid a single white envelope across the counter, winked, and slowly turned toward the exit.
Now, all I had to do was wait and hope he showed up.
I sat patiently near the apartment window, tapping my crop against my boots. The laces were tied tightly, just the way I liked them. My black vinyl crotchless panties came up above my belly button, accenting my curves and hiding the less desirable parts. I spread my legs to air out my pussy. I had masturbated earlier just in case Christopher bailed on me, so my cunt was already aroused and ready for more. The straps of my bra covered my entire chest, up to my neck where they choked me slightly. Holes in the bra exposed my large, long nipples. I wondered how much Christopher could handle? How much pain, how much teasing, how much woman?
Just then, I heard a tiny knock at the front door. Holy fuck, he actually came.
I stood up quickly, adjusted my outfit and walked toward the door.
“Who is it?” I called teasingly.
Of course I knew who it was. It was the stroke of midnight, just as I had instructed. This was a good sign. It meant Christopher knew how to follow directions.
“Um.. it’s me. Christopher. From the coffee shop. Freshly Ground. Um, you came into the shop earlier today…”
He was still stuttering nervously when I opened the door. He looked a little different standing there, without his green apron and visor — younger, almost. He wore a white and blue plaid shirt, jeans, and loafers. He stared wide-eyed at me. His mouth gaping open in surprise. I didn’t speak. Just stood there letting him take it all in. Before he could make a sound, I reached over with my whip and pushed his bottom jaw closed. Then, beckoned him inside with a single finger.
I could feel his eyes roaming my body. I turned around abruptly, causing him to run directly into me. His small frame bounced off my supple breasts. I smiled and slowly picked up a collar and chain from the nearby table. He went to speak but I quickly stopped him, pressing my finger firmly against his lips.
“No talking, remember? Did you read the note? The entire thing? Nod if you did.”
Christopher’s head slowly moved up and down.
“Good.”
I moved my finger from his lips and shoved his head downward so I could attach the collar. Once it was securely in place, I connected the chain and wrapped the leash tightly around my hand. I turned and tugged on it, dragging him behind me.
As we entered my sex dungeon, the warmth and scent of the candles overwhelmed me. I stopped briefly, closing my eyes and inhaling both the smell and the sensation. It’d been far too long since I used my dark playground. The large, heavy wooden bondage table sat in the center of the room. Beside it was a chair and a cabinet filled with all my favorite toys. The elaborate sconces on the walls glowed brightly with warm, rising flames.
I heard Christopher squirm behind me, breaking my concentration. I turned to him abruptly and he jumped back.
“Get undressed,” I commanded.
He just stood there, staring at me.
“Did you hear me? Get the fuck undressed. Now. And don’t make me wait.”
I stood there impatiently and watched as the inexperienced boy before me scrambled out of his clothing. After only a few seconds, his shirt, pants, and shoes were in a pile on the floor beside him.
“Stand up straight!” I cried.
Christopher’s posture instantly changed, as he squared his shoulders and puffed his chest. He was skinny, with minimal muscle definition and pale, white skin. He was also hairless, like one of those strange Sphynx cats. My eyes traced his body until they landed on his crotch. He still had his underwear on and beneath the thin gray fabric of his boxer briefs I could see a fully erect, long, thin penis. A few drops of precum stained the light material. I smiled devilishly. I knew he was well-hung. I had a knack for picking out the young ones with the big cocks. I bet he had no idea what he was even capable of or how to work his tool. But I’d show him.
“Take them off,” I instructed, tapping his shaft.
He hesitated, but only for a second before slowly dropping his underwear to his ankles and kicking them off to the side.
I gasped in wonder and delight. His cock was beautiful. Long, thin, uncircumsized. I licked my lips but held back the urge to reach out, grab it, and shove it in my mouth. I gathered myself and pointed to the table.
“Get on it.”
I followed Christopher over to the wooden table, the chain still in my hand. He slowly mounted it and waited for his next direction.
“Lay down and put your hands in those cuffs.” The table was already rigged with restraints — two at the top and two on bottom.
He slipped his thin wrists and ankles into the shackles and I tightened them. I slowly walked around the table, running the tip of my crop over his young, tight body. His cock twitched and bounced slightly.
“Are you aroused, Christopher?” I asked with amusement in my voice.
He was about to answer when he remembered the rules. He stopped himself and nodded, instead.
“Christopher,” I continued, “Have you ever eaten pussy?”
He didn’t move for a moment but then slowly shook his head.
No? No?! This was fucking perfect. I’ve never had a first-timer. I mean, I’ve fucked plenty of virgins but they’ve all at least eaten a cunt once in their lives. This was uncharted waters for us both.
I climbed onto the table and mounted his thin body. My pussy was already dripping in anticipation. It sat inches from his cock. So close the walls of my cunt throbbed, begging me to give-in and slide that long, beautiful cock into my hole.
No! I wouldn’t. I couldn’t. Not yet.
I moved my body upwards and sat gently on his chest. My wet pussy lips spread, leaving a gooey pile of cum between his nipples.
“You’re going to eat my pussy, Christopher. I’m going to sit on your face and you’re going to lick and suck me until I cum. Then you’re going to drink every last drop of my pussy juice. Do you understand me?”
Christopher’s eyes were wide. I couldn’t tell if he was nervous or excited. Not that it mattered much. Before he could respond, I pulled my body up another few inches and straddled his face. My clit was inches from his mouth.
“Lick it. Slowly.” I instructed.
I braced myself over his head and waited. It only took a few seconds for his tongue to make contact with my clit. He pushed the tip into my nub and then removed it.
“Again!” I yelled. “But this time, don’t stop so soon. Lick it in small circles until you feel it get hard.”
His tongue made contact with my body again as he slowly swirled my clit, just like I told him to do. I felt it begin to swell. Blood was rushing to my pussy now. I moaned slightly and felt his tongue pick up speed.
“Oh yeah, just like that.”
I began to slowly rock back and forth on his face. I heard the chains rattle as he desperately tried to release his hands. I reached up and squeezed my tits. I loved hearing them struggle and squirm.
His tongue found my honey hole and began lapping up my pussy juice.
“Yes! Yes! Fuck it. Fuck my hole with your tongue.”
Christopher strained to bring his mouth closer to my cunt. He thrusted his tongue upward, inside my body. I started bouncing up and down on his face, driving his tongue deeper. My knees dragged against the wooden table surrounding his head. I leaned down, bracing myself on his wrists, pinning him down even harder.
“Fuck yeah. Eat that pussy.”
I rubbed and grinded my wetness all over his face before planting my pussy back on his mouth. His nose jammed into my clit while his tongue spread my lips and fucked me. I could hear him moaning and gulping down my thick pussy cream. The sounds were muffled by my fat cunt. I pushed down harder. I wanted to cum. I wanted to fill his mouth and throat with my juices.
“I’m gonna fucking cum in your mouth, Christopher, and you’re going to eat it all, you hear me? Do you hear me?” I yelled.
He feasted eagerly on my cunt but I felt him nod his head beneath me. I slid back and forth, my clit swollen with desire. Just as I felt the rush of climax take over me, I stopped. I stopped moving my body and let Christopher make me cum. His tongue worked my lips and hole feverishly. He jammed his nose into my clit and sucked my lips into his mouth.
“Oh my God.. Oh my God…”
I spread my knees wide and unleashed a long, steady stream of warm cum directly into his mouth and down his throat. I heard him moan, gag, and gulp as he drank down my tangy gift. He continued to lick me until my body stopped shaking. Even after I had finished, he continued to slowly work his tongue in and out of every crevice, lapping up every last drop.
“Good boy,” I said, tugging on his hair.
After a while, I finally removed my pussy from his face. His chin, lips, and nose were covered in my cum. It glistened in the flames that surrounded us. I moved my body to one side of the table and grabbed his cheeks with one hand, squeezing them together until his lips pursed like a fish. Then I leaned over.
“Stick out your tongue.”
He did as he was told and I sucked my sweet juice from it. I traced his lips and licked his cheeks before letting go.
He laid there with a content look on his face. I was pleased to see he was still fully erect. I grinned.
“You did good, Christopher,” I said as I stood up beside him. “Maybe next time I’ll let you fuck me.”
And with that, I exited the room and closed the door.
She was the best part of my day. Working at the coffee shop wasn’t exactly my dream job but it paid for gas in my car and nights out with friends. Most of our customers were stuffy businessmen and giggly teenage girls that ordered smoothies and chocolate chip cookies. But not her. She was different.
I greeted her with the same standard phrase all employees used: “Welcome to Fresh Grounds, would you like to try…”, and then I’d rattle off whatever that week’s must-have drink or bakery item was. She never accepted my offer. She always ordered the same thing. A medium coffee with almond milk and one sugar.
I didn’t even know her name but I secretly fantasized about her. She was one of my favorite go-to images when masturbating in the shower. I’d picture her toned legs wrapped around my stomach while I fucked her. Her huge tits suffocating my face, my mouth grabbing for her nipples. I always wanted to fuck an older woman. They’re experienced. They take charge and get the job done right. Too bad I was too much of a pussy to do anything about it.
Then, one day, the unthinkable happened. She came in at the same time she always did except today, she looked different. She looked even more irresistible than most days. Her tits were nearly in her throat and her skirt was tighter than ever. The red silk blouse she wore screamed “sex”. I was instantly hard.
As she approached the counter I shifted in place, trying to move my now bulging erection to a more comfortable position beneath my cheesy green apron.
“Hello, welcome to Fresh Grounds. Would you like to try one of our freshly baked orange and cranberry scones?”
I knew she’d say no like she did every day. I was just about to enter her coffee order into the register when she said, “No coffee for me today, thanks.” She slid a white envelope across the counter, winked, and left.
What the fuck? I grabbed the envelope and shoved it in the front pocket of my apron, my heart pounding in my chest and my cock throbbing in my pants. Had anyone noticed? My mind was racing a million miles an hour. What could be in the envelope? Was it a naked picture? An invitation? A restraining order?
I couldn’t wait until the end of my shift to find out. I excused myself to the bathroom, locked the door, and hid in the stall for some privacy. I tore open the envelope. It smelled like her. The scent filled my nostrils as I slipped out a small piece of paper and unfolded it. It was a note.
Tonight. Midnight. Don’t be late. Don’t speak. You won’t be disappointed.
Beneath the handwritten words was an address and a signature that read Mistress M.
I sat there motionless for a few seconds, staring at the paper in my trembling hand. I was confused and extremely aroused. Mistress M? Is that some sort of stage name or code word? I looked at the address again. It was close. Should I go? Was I going to be sold into some bizarre sex slavery? I shook my head. Don’t be ridiculous, Christopher. She just wants you to come over for…. for… I couldn’t come up with anything logical to finish that sentence. So instead, I shoved the note into my pocket, tossed the envelope into the trash, and headed back out to finish my shift.
That was the longest 4 hours of my life. All I could think about was Mistress M. Her invitation, her gorgeous tits, her full lips, and that tight skirt. I was semi-hard all day, consumed by the thought of going to her apartment for whatever she had planned. You won’t be disappointed. That part of the note stuck out in my mind most. That’s it, I thought as I started my car and headed home to jerk-off in the shower, I’m going.
It was 11:53 p.m. and I was sitting outside the address on the note. I clutched the paper tightly in my hand, staring at the thin, black writing and back up at the tall, looming apartment complex. There was no question this was the right place. The only question that remained was if I had big enough balls to actually go inside. I’d never been with an older woman. A few quick fucks in college and a handful of blowjobs were the extent of my sexual portfolio. Would I embarrass myself? Based on the note, I was pretty sure Mistress M would be the one calling the shots and I was just along for the ride (literally). I swallowed hard, pushing my nerves aside, and headed for the door.
It was midnight on the dot when I knocked on the door. My mouth was dry, my palms were sweaty and my cock was hard for what felt like the 20th time that day.
“Who is it?”, I heard her seductive voice through the thick wood door.
I didn’t know how to answer and instantly started fumbling over my words.
“Um… it’s me. Christopher. From the coffee shop. Freshly Ground.” I sounded like such an idiot but I couldn’t stop my voice from shaking. “Um, you came into the shop earlier today…”.
I was surprisingly relieved when she swung the door open since it stopped me from stuttering like an idiot. But that sense of relief was instantly replaced by complete awe and arousal. There she was, looking the best I’d ever seen her. My mouth hung open as I scanned her curvy figure.
She wore boots tied up to above her knee. Her muscular body was covered in vinyl — everywhere except her erect nipples which hung like two long torpedos begging to be sucked and tweaked. My dick was pressing uncomfortably against my jeans. I did a mental check of my own outfit and felt instantly regretful. I was wearing a plaid button-up shirt. Like the kind you wear for your grade school class picture. What a loser. But before I could dwell on my attire any longer, she closed my open jaw with the tip of her crop and invited me inside with a single, seductive finger.
I watched her toned ass as I followed close behind her. Too close, as it turns out since she stopped unexpectedly. As she whipped around, we stood face to face, my chest pressed against her bare tits. She reached for what looked like a leash and collar sitting on a nearby table. I swallowed hard wondering what I had gotten myself into and if it was too late to back out. Then, I gave myself a reality check. Don’t be a pussy, Christopher. This is a once in a lifetime opportunity. Your buddies would kill to be in your position right now so suck it up and brace for whatever’s ahead.
I wanted to say something. To ask her if I should put on the collar but she stopped me, pressing her finger against my half-parted lips.
“No talking, remember? Did you read the note? The entire thing? Nod if you did.”
I nodded, recalling what the note said. Don’t speak.
“Good”, she said simply.
She pushed my head down, placing the collar around my neck and grabbing firmly onto the leash. I couldn’t help but move forward as she dragged me toward her. The collar felt surprisingly good around my neck. She stopped at a black door at the other side of the room. I instantly felt warmth and smelled candles burning as she pushed it open. She pulled me inside, closing the door behind us and giving me a moment to scan the room. My eyes instantly landed on a large wooden table in the center of the room, complete with chains and shackles. Oh fuck. Was I ready for this?
Sconces burned fiercely on the walls and a table nearby was covered in what looked like modern torture devices alongside oversized dildos. I swallowed hard. My mouth was dry and I was sweating profusely.
“Get undressed,” she demanded.
I stared back at her, unable to move and not allowed to speak.
“Did you hear me? Get the fuck undressed. Now. And don’t make me wait.”
Oh shit. She meant business. I slipped off my shoes using my heels while simultaneously undoing my pants. They dropped to the ground and I kicked them off as I unbuttoned my shirt and let it fall to the floor. At that moment I was thankful for the heat from the sconces and felt Mistress M’s eyes scanning my body. I wish I’d hit the gym more often as I imagined her disappointment with my weak, thin frame. I glanced down and realized that my erection was in full-view.
She tapped the tip of my cock with her crop. “Take them off.”
I slid the tight boxers off and tossed them aside, straightening my back and trying to appear much more confident than I felt. Her eyes scanned my body as she licked her lips. I felt a rush of pleasure. She seemed pleased with what she saw. But her smile was fleeting and quickly replaced by a more stern demeanor.
She pointed to the large wooden table.
“Get on it.”
She walked me over to it like a dog on a leash and I climbed up. It was hard and rough against my bare skin. There were shackles at the top and bottom. I was breathing heavily now, equal parts excited and nervous.
She instructed me to lay down and put the restraints on my wrists and ankles and I obeyed, feeling exposed and vulnerable. My cock was still rock hard, resting straight up against my belly. She slowly walked around the table, running the crop over my arms, legs, and stomach. My shaft was twitching with desire.
“Are you aroused, Christopher?”
The sound of my name on her lips made my dick throb and my nipples perk up. I was about to answer when I remembered the rules and nodded instead.
Her next question made my heart stop.
“Christopher,” she continued, “Have you ever eaten pussy?”
Fuck. The only thing I’d never done was eat pussy. It’s not because I’m afraid to do it or grossed out by it. I’ve just never really had the chance. Most of my sexual experiences up until this point involved lots of drinking and awkward sex in the back of a car or in a closet at a party. I never had the opportunity to properly lay a woman down and explore her most intimate areas with my tongue, but I sure have thought about it. About making a girl come over and over again. About tasting her sweet pussy cream. But now, I was just embarrassed. I had to admit I’d never done it before. Lying to Mistress M didn’t seem like a good idea but if I told the truth she’d probably think I was pathetic. I didn’t want to make her wait any longer so I reluctantly shook my head no.
To my delight and surprise, she seemed pleased by this. With a sly smile, she climbed onto the table and straddled me, plopping her wet pussy directly on my chest. It was then that I realized her panties were crotchless. I felt her warm, soft folds spread across my chest. Her beautiful full ass was only inches from the tip of my dick and I had to stop myself from thrusting my hips upward, begging to fuck her.
Then, she spoke.
“You’re going to eat my pussy, Christopher. I’m going to sit on your face and you’re going to lick and suck me until I cum. Then you’re going to drink every last drop of my pussy juice. Do you understand me?”
Man, she cut right to the chase and I fucking loved it. Being instructed to eat a beautiful woman’s pussy was like an erotic fantasy come true. I didn’t have much time to think. The next thing I knew, Mistress M was squatting over my face, her eager wet pussy just inches from my mouth. I closed my eyes and inhaled. She smelled sweet but pungent. The room was dark so it was difficult to see every fold of her cunt. I’d have to trust my instincts.
“Lick it. Slowly,” she instructed.
I obeyed. I extended my tongue out until it made contact with her soft, wet lips. I found her clit instantly. It was fat and round. I flicked it a few times with the tip of my tongue.
“Again!” She yelled. My neck was straining to make contact with her body. I was hungry for it now.
I arched my shoulders, getting a better angle as I began swirling my tongue around her nub. It began to harden slightly. My nose was nestled into her bush as I continued to work her clit and press her lips open with the flat part of my tongue.
“Oh yeah, just like that.”
Her words of encouragement made my cock throb. Her cunt was producing an abundance of thick, sweet cream as I explored every fold and crevice. I pulled on the restraints, wanting desperately to cup her full ass with my hands and shove my face completely into her pleasure zone.
She began to move back and forth, slowly and methodically riding my tongue and mouth with her cunt. She was pinching her own nipples now as she ground against my face. I could barely breathe but I didn’t care. Her sweet juice on my tongue was like honey and the smell of her femininity filled my nose and throat. I moved my tongue down, shoving it into her gaping hole. Her back arched and she pushed down harder, willing me to tongue-fuck her.
“Yes! Yes! Fuck it. Fuck my hole with your tongue.”
She cried out as she bounced on my face, squeezing her tits and fucking my tongue like it was her personal pleasure toy. Who was I kidding? That’s exactly what I was and I was loving every fucking minute of it. My dick had never been this hard. I thought I might come just from the combination of chains, candles, and the intoxicating feeling of being completely at her mercy.
I couldn’t get enough as she continued to cry out, “Fuck yeah. Eat that pussy.”
“I’m gonna fucking cum in your mouth, Christopher, and you’re going to eat it all, you hear me? Do you hear me?” She was yelling now.
I couldn’t have answered even if I wanted to or was allowed. I was completely engulfed in her cunt now. Her cream was all over my face and chin. My mouth was filled with every inch of her pussy. I struggled to swallow the thick, creamy juice that her body was producing. It coated my throat like a warm, soothing elixir.
Just when I thought she was about to finish, she stopped moving. Stopped grinding against my face and instead let me do the work. I sucked her clit between my teeth, nibbling and flicking it with my tongue. I switched from sucking on her clit to fucking her with the fattest part of my tongue. I feasted on her delicious pussy, willing her to come. And then she did. A fresh flood of hot, creamy jizz gushed from her gaping hole and filled my mouth. I gagged slightly as the sweet juice glided down my throat and into my belly. Her knees slammed against my shoulders and head, squeezing every last drop of cum into my mouth.
Even after her body stopped shaking, I left my tongue in place. Slowly and methodically running it up and down her folds, being careful not to touch her now over-sensitive clit. I softly kissed her labia and the edges of her lips.
She tugged my hair firmly and called me a good boy. I laid there with a content smile on my face, which was now covered in a thick layer of pussy cream. She dismounted me and grabbed my face firmly like a stern mother ready to scold her unruly child.
“Stick out your tongue,” she demanded and I did as she asked.
To my delight, she leaned down and sucked my tongue, sharing the taste of her sweet nectar. Her tongue moved from my mouth to the outer edges of my lips and even my chin and cheeks as she helped clean herself off my face.
My cock was still throbbing but for the first time in my life, I felt sexually satisfied in a different way. Making Mistress M climax was almost as arousing as having my own orgasm.
“You did good, Christopher,” she said with a softer tone than before. “Maybe next time I’ll let you fuck me.”
I heard her heels on the floor and the door closing. She was gone. I didn’t move. I couldn’t move. But at that moment, I didn’t care. I laid there, enjoying the heat of the flames on my naked skin and the lingering scent of Mistress M’s pussy on my face.
