The Mistress from Petaluma

For a long time now, I've fantasized about being dominated. I'm what you would call a "weird" kid; awkwardly tall and skinny and nervous in social situations. I've had a couple of girlfriends, sure, but the small amount of sex I've had has been vanilla at best. Then one night about a year ago, after smoking a couple of bowls and looking up random porn on the internet, I stumbled upon a page titled "Femdom." The first video got me harder than I can ever remember. I must have cum a dozen times that night. By the time the sun was rising, I was watching women force men to wear panties and get fucked by strap ons.

This new fetish finally led to my creeping on BDSM personal sites. I usually stroked myself while reading the personals, but a week ago I finally posted an ad: "19, first time sub M seeking dom F." I included a full body shot of me naked from behind. My face was hidden by my mop of shaggy blond hair. The flash from my phone made my slender back look extra pale - it arched down to my round ass. I thought about spreading it open but decided against it in the end.

I guess my body is a gay man's dream - I got HUNDREDS of replies from men despite my ad specifically indicating I was seeking a woman. While annoying, it was flattering to be wanted. I read every single reply, and got hard reading about all the things all these would-be doms would do to me: "I'll tie you down to the bed and spank those ass cheeks until their red and burning, then lube up your tight little hole..." "I'll force you on your knees and slap your face until you left your mouth gaping open, then I'd slide my hard cock all the way down your throat..." "I'll dress you up in my wife's clothes and make you dance for my friends during our poker game."

It was the next day when I received Mary-Anne's, I mean, MISTRESS'S, email. It was short and to the point: "You are pretty. I am currently seeking a submissive to train for my pleasure. Send me a face picture and your phone number if you are serious." Unlike the many, many cockshots I had seen with the other replies, she hadn't attached any photo. I reread that email dozens of times, with a giddy nervousness in the pit of my stomach. I had no way to know this wasn't another man, or some scammer who wanted to match a picture of my face with my previously posted nude who could then threaten to show it to my family if I didn't pay some ridiculous amount of money! However, the next day the excitement of "this could be real" won out, and I replied to her message, along with a selfie and my cell phone number.

The first time she called I was sitting in class. After class I listened to the voicemail she left: "That is your first strike. The third time you disappoint me, our relationship is finished."

I texted her back immediately, "I am so sorry, but I was in class. I'm headed to my next class now."

She waited 20 minutes before texting me back. I snuck a peek at my phone as my professor lectured about linear equations. "If you don't call me in 5 minutes, don't bother trying to contact me again."

My mouth went dry, but hastily I slid out of my desk. The professor actually stopped his lecture and sarcastically said, "Class, PLEASE try to fit your restroom breaks in the period of time BETWEEN classes."

She picked up on the third ring. "Three minutes and forty-six seconds - cutting it close, aren't we slut?" Her voice was harsh and high pitched, and left me breathless. "One of my sissies has decided to end our relationship," she continued matter-o-factly, "I enjoyed your picture, and I'd like to see if you'd make a good fit for the position." She interviewed me for twenty minutes as I stood in the hallway, my mind half worrying about making a good impression and half worrying about the calculus class thinking that I was constipated. I didn't learn that much about her, other than her first name, that she was divorced, and she lived a two hour drive away from my college campus.

However, I answered every one of her probing questions: "No, I am not a virgin. Two girls. A man? No, never! No, I've never put anything in my asshole. I've never sucked one, but my friend Jerome and I used to watch porn and masturbate together in high school. I've never touched one, though." When I finally made it back to class, I had a small dot of precum leaking onto my jeans.

After the first phone call, she put me through a series of "tests" to prove that I was loyal to her. I had to go to Victoria Secret and buy a pair of panties (I had to send her a picture of the receipt) then photograph myself wearing them in various poses. I had to go to a sex shop in downtown's "gay district" and make a voice recording of myself asking the (male) shopkeeper about which dildo would be best for a beginner. Finally, we video chatted - she had her face hidden, but she had me be her "little camgirl." After I came, she had me smear my cum on my face then smile for her - over my computers speakers I heard a small "click" of a screenshot being taken.

It was then, with my cum dripping down my cheeks, that she sent me her address and ordered me to be there the following evening. The two-hour drive felt instantaneous - I'd smoked a joint before I left but even that couldn't quell the butterflies in my stomach, and my sweaty palms made the steering wheel slick beneath them. Her address was in an upper class suburb. I parked on the curb in front of her driveway. Her home looked normal enough: single story, overgrown lawn, older minivan parked in the driveway despite a two car garage.

After an eternity of waiting, I got out of my car and walked up to the door. It was unlocked, like she said it would be. I let myself in and slid the deadbolt behind me, as ordered. A short hallway led me to the living room where I found her sitting on a velvet couch, a glass of red wine on the table beside her, reading a book. I realized that this is the first time I've ever actually seen her: She had a few wrinkles across her forehead and jet black hair with streaks of white in it that tumbled down across her shoulders. Her skin was a light brown. She wore a large, red robe that hid her legs, which were tucked underneath her.

She put down her book and regarded me as I entered. "Well, hello there... Dillan, is it?"

I tried to swallow, but my mouth was dry. "Yes... yea, that is me. Mary-Ann, right?"

She shook her head, her full, red lips turning downwards into a frown. "Haven't I told you that you are ONLY to refer to me as Mistress?"

A small shaking started in my legs. I had no response.

She tossed her book onto the side table, picked up her wine and took a sip before sauntering towards me. "I'll let THAT one slide, but don't forget little sissy, you already have disappointed me once. And what happens when you get to strike three?"

She stopped in front of me. I am a full foot taller than her, yet I felt like she was towering over me. "I um, I can't see you anymore?" I stammered.

"That is right, little sissy. Now. Let's have a look at you. Clothes off!"

I froze again. Was she serious? I'd been here less than five minutes, and...

"Do you SERIOUSLY want to get to strike two now?" She raised her voice as she scolded me.

"Um, no Ma..., um, Mistress."

"Then get your clothes on the floor, NOW!"

Quickly and clumsily, I slid my shirt over my head. My small, pink nipples grew hard in the sudden cool, and a tingle flew up my spine. I kicked off my shoes and unzipped my jeans, sliding them down. Underneath I was wearing the sheer red panties that I bought for her first test.

"Stop," she commanded as I stepped out of my jeans. "Did I tell you to wear those panties tonight?"

"No, um, Mistress. I just thought that, um... I thought you'd like it?"

Her dark eyes looked deep into mine, "Do you like the way the lace feels against your skin?"

"Um..." I fought against the nervousness. I fought the inexplicable urge to lie. To be a man. "...yes, yes they feel nice."

The volume of her voice fell some, "Do they make you feel pretty?"

A hot rush of blood filled my cheeks. All I could do was nod. This made her laugh. "You just might do. Well then, you can leave those on for now. Come on, hurry up, get those ugly socks off!"

A moment later and I was only wearing the panties. The see-through rear slid into my butt crack, feeling like a thong, leaving my smooth white cheeks exposed. My cock is hard and too big to fit inside the panties' thin, sheer crotch, so it hung out of one side, a thread of clear precum hanging off of my swollen purple head. The wrinkles around my Mistress's eyes turned up into a large smile. Her teeth were perfectly white. With one hand she grabbed my cock and pulled me closer to her, like a dog on a leash. When I could feel her breath on my neck, she squeezed my penis hard enough that I whimpered.

After a moment her grip loosened, and she softly stroked me. "Has anybody ever told you that you have a giant fucking cock?" She asked as one of her fingers explored underneath my foreskin, twirling around my engorged head.

I felt like I was going to cum all over her hand. "Um..." Both girls I'd been with had told me as much, but I thought they were just being nice. Of course I'd seen other guys' dicks in gym class, but the only time I've seen hard cocks were in porn and that one time in high school, so I guess I didn't have any sort of realistic comparison. "...I, I guess?"

She brought her precum covered finger to my lips and forced them inside my mouth. Without being told, I sucked on her slimy digits, tasting my own salty fluids. "Well, you do have a big one. Let me tell you, Dillan. I've had several sissy subs over my years, and EVERYONE wants to please me, and they try their damndest I tell you. But this..." She roughly grips my penis again and smirks as I try to contain my discomfort "...well, you are going to make a fun little toy for mommy."

Penis in hand, she led me down the hallway to a door with a lock on it. From around her neck she lifted a small chain with a key on it, and slid the key into doorknob. Before turning the key, she turned around, looked up at me, and said, "This is your last chance to back out, Dillan. Once you come downstairs, you belong to me." She turned the key and swung open the door. Behind it steps led down to a dimly-lit basement. "Well?"

I took just one second to decide, then walked through the doorway.

...

At the bottom of the stairs, Mistress flicked a switch and the basement was flooded with light. It was lined with a thick, black carpeting that tickled my toes as I walked on it. Stocks stood in one corner of the room, next to a large wooden X that had leather cuffs on its extremities. Along the walls were shelves that displayed a wide variety of whips and paddles. In the corner of the room, a large black chest stood. In the middle of the room was a tall bed with four posts, and above it metal rings were bolted into the ceiling, a few of them with chains hanging from them. The bed was about 3 feet off the ground, and a cage with flat iron bars was built beneath it. What made me most nervous, however, was the was a huge flat-screen TV mounted on the wall and the camcorder on a tripod in front of it.

Mistress led me to the foot of the bed and pushed me down onto my knees before dropping her heavy robe to the floor. She wore a leather corset, black lace thong with garters, and black fishnet stockings. Her giant breasts couldn't be suppressed by the corset - they spilled out over the top of it. Her hips were wide and her ass stuck out like a second set of breasts behind her. She was at least 20 pounds overweight, and her belly and love handles pouched out of every opening on the corset. Each asscheek jiggled as she walked over to the wall and selected a soft leather cat-o-nine tails and walked back towards me.

"Your name is not 'Dillan,' anymore. Your name is now Jessica." She bent at the waist so our noses almost touched. "What is your name?"

"Jessica."

This made her smile. "That's a good little sissy." She flicked the cat-o-nine tails through the air gently, the leather straps making a soft "whoosh" through the air. She continued, "Your life outside of this place is not as important as my pleasure, is that understood?" I hesitated before nodding. "As you know, the third time you disappoint me, you are out of here, and you never get to visit this place again." Her wrist suddenly snapped the whip in a violent lash against my chest - several streaks of burning pleasure manifested between my nipples.

"I don't use 'safewords.' If you ever don't want to be a part of bringing me pleasure, you can say one thing - 'I quit.' This will count as your third strike and you will be banished from my life forever. Understood?"

I nodded again.

"I see you looking at the camcorder over there - don't worry, the videos I record are MOSTLY for my own enjoyment. Occasionally if I make something that is particularly hot I'll share it with a few of my friends or watch it with my other sissies. I'll never put anything on the internet or anything. That being said..." she picks up a remote control and pushes a button. The screen fills with a high definition picture of my smiling face, covered with cum. "... don't even THINK about trying to take advantage of me. Do you understand?"

"Yes Mistress," I replied immediately

"That's a good girl," she said with a smile. "OK, Jessica. Get on the bed. I want your face down with your ass sticking up. Now!"

I did as I was told immediately. The bedspread was soft against my chest and smelled freshly washed. I stretched my arms out and arched my back so that my buttcheeks were held high and spread open. I felt a finger slide my panties down, leaving them halfway down my thighs. A soft breeze caressed the sensitive skin of my naked anus as Mistress blew against my most private place. "Jessica, you have the NICEST ass, and the cutest little asshole!" I gasped and then moaned into the bed as her warm fingers gently rubbed the skin around my sphincter in little circles, each revolution with a bit more force than the last. "You said you've NEVER had anything inside of here?"

It's hard to open my mouth without making a noise of pleasure, but I try my best. "N.. no...ummh, no Mistress."

I can feel her smile as she continues to massage the entrance to my hole. "Tell me your name, sissy."

"It's Jessi-" A yelp cuts off my reply as she suddenly shoves her dry finger a centimeter inside of me. "Oh... Oh god..." I mumble. The sudden intrusion of her digit felt like a hot little coal inside of my ass. The heat became more and more intense as my asshole reflexively clenched against her finger. I tried to pull away, to lay flat on the bed and get away from the burn that was opening me up, but she held onto my hips and kept me where she wanted me. "Fuck, oh fuck it hurts! It hurts!" I whimpered into the bedspread as I did my best to hold still.

"Shh, shh... there, there now baby girl," She stroked my lower back while keeping her finger inside of me. "I'm sorry, Jessica. That wasn't very nice of me - I should've used lube for your first time. But you have the PRETTIEST little pink asshole and I just had to pop your cherry right away!" Keeping her finger still, her other hand moved from my lower back to my cock. She wrapped her hand around me - I was rock hard. "Oh, but somebody likes this!" She exclaimed as she slowly began to stroke me, "you're making a mess on the bed!" I looked down between my legs - it was true, my penis had become a faucet, gushing precum onto the black bedspread.

"That's it, baby girl. You love it! Relax!" I tried to do as she said, but her finger still felt like a hot poker inside of me. "I'm barely past my fingernail. You're going to be taking a lot more than this before long." With no warning, she popped her finger out of me, leaving me empty with a residual warmth inside my rectum. Helplessly I slid onto my belly, breathing heavily. My cock was forced down between my legs, and Mistress's fingernails were softly scratching up and down my shaft.

"Fuck it!" She said as she got up and walked to the large, black chest and opened one of the smaller drawers. "Jessica, I'll have you know that it is a HUGE reward for a sissy slut like yourself to have her cock inside of a goddess like me. Under normal conditions, it would take MONTHS for you to get to feel my pussy. But honestly, you have one of the biggest dicks I've ever seen."

She returned with a condom wrapped in golden foil. "Get on your back, sissy." I did as I was told, my penis standing straight up in the air. She slid her thong down her legs, leaving the garters and fishnet stockings. She climbed up onto the bed and brought her ass down onto my face. Her vagina was fat with large lips that hung down and tickled my nose. She had thick curls of black pubic hair that surrounded her labia and snuck to her asshole.

"Get me wet, you little slut," she commanded. I opened my mouth and pushed my tongue up as far as it would go. I probed inside of her pussy, licking up and down. She tasted rich and smelled like raspberries. Suddenly, I heard the sounds of moaning and a rhythmic slapping - she had turned the TV on and was watching porn as she straddled my face.

"Don't TELL me you don't know how to eat a woman out, Jessica!" she exclaimed after I licked her for a minute. "Just because YOUR clitoris is so easy to find! Those poor girls you dated... I'll let you try a little bit longer."

On the screen, four large black men surrounded a petite white pornstar. One of them fucked her ass while she struggled to put the other three cocks in her mouth. The camera zoomed in on her lips, stretched over a giant, black penis. Drool fell out of her lips and onto her heaving chest.

"That's it, Jessica - I'll teach you how to eat pussy another day. For now, mommy has got to do things herself - you will be punished for this!" She dropped her hips down onto my head, her pussy covering my mouth. She began to grind herself against my lips and tongue. My nose was pressed against her asshole. I realized that I could not breathe. I tried to continue to lick but after a few seconds, the panic of the air hunger began to kick in and I became genuinely afraid of suffocating. Just as I was about to hit her thighs, she lifted her pussy off of my face.

"No teeth now, Jessica. Mommy will be ready in a minute. Don't you DARE let this cock get soft while you get me ready!" And she smothered me again, rubbing herself all over my face. I could hear the pornstar moaning on screen, with four deep voices calling her slut, telling her to take their cocks. The pornstar started to scream when one of the entered her pussy while his colleague was still inside her ass.

After a few more air breaks, Mistress's pussy started to drip onto my lips. When she was riding me, I had to swallow her juices, which began to drip down my cheeks and up my nose when my mouth was too full. Finally, I felt her putting a condom on me while she sat on my face. Once it was in place, she stood above me and turned around. She laughed at my slick face, covered in her juices, "It didn't take you long to turn into a filthy whore, now did it?"

I didn't know how to respond, so I just smiled.

She lowered herself onto my cock. I watched as her labia slowly parted to accept my head and slide down my cock. Her warm walls caressed my shaft. When her hips met mine and I was completely inside of her, the feeling was overwhelming. Too much. I had been hard for at least half an hour, and Mistress's pussy felt so good. Before she could slide up on my cock and begin fucking me, I felt myself cum. I couldn't stop it. It was the best orgasm I've ever had - The stream of cum shooting out of me was a river of pleasure that traveled down my legs and up to my brain. I saw stars. A gentle buzzing filled me ears for a moment.