Brittany's Strapon Hell Week 01

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Brad is taken by her strap-on class.
2.5k words
3.96
100.5k
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Part 1 of the 5 part series

Updated 11/01/2022
Created 05/03/2006
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*

I had just joined the mile high club with Mistress Angelina Jolie, though not in the way you would think. She had violated me with a fist-thick strapon in the airplane bathroom, then paraded me in front of the other passengers back to the first class area, which was full of mistresses.

Thinking back on it, I had also reached a new level of submission on that plane ride. I had knelt beside the woman who had just fucked my ass, and without being ordered, had learned over and taken her cock in my mouth. I recall at the time, only wanting to please my mistress as I bobbed shamelessly on her shaft, to the amusement of the other mistresses.

We had just arrived at the hotel, and Mistress Brittany and I went up to our room. She commanded me to clean up, which I quickly did. I presented myself to her naked, head bowed, hands clasped behind my neck. "Oh princess, you've had a rough day. You deserve a treat," she exclaimed. "I think I will allow you to lay next to me in bed tonight. Do not be confused, you are not sleeping with me. I only sleep with men, and trust me, you are not a man," she laughed as she playfully batted my tits. I slowly drifted off to sleep, elated to be in the same bed as my mistress.

A few hours later I was awakened to sharp pain in my nipples. Mistress had decided to wake me by giving alternating sharp bites on my sensitive nipples. As much as I wanted to scream out, I bit my tongue and took my punishment. "Good morning slut. Here's the plan. Go in the bathroom and prepare yourself as I have instructed. I have to get ready myself.

With that I minced to the bathroom, careful not to rub my sore nipples in her presence. I found a bottle of self tanning lotion, which I spread evenly over my entire body, turning myself a dark shade of tan. A bottle of hair dye sat on the bathroom counter, and ten minutes later I was a stunning brunette. To my surprise, there was a matching set of black lingerie on the bed, which consisted of a bra, thong, garter belt and thigh highs. I hardly ever got undergarments.

"Oh, baby, I almost forgot. You are going to need some help," Mistress said, as she came into the room. She laid me down on the bed, and pulled out a roll of tape, which matched the new color of my skin. She gave my little cock a few quick pumps, and then taped it to my stomach. A few layers of tape later, my cock and balls were completely taped to my stomach, leaving a smooth, seamless appearance. I was then left to do the rest myself.

The bra was no problem, as I was well versed in putting one on (though I seldom got to wear one). Next, came the garter belt and thigh highs, followed by the thong. Every slut knows the thong goes over the garter belt. My outerwear consisted of a ribbed turquoise sleeveless turtleneck blouse, which really made my huge tits look even bigger, and a short, belted black skirt. Black, six inch platforms completed the look.

Mistress reentered the room dressed in a tight pair of jeans, and an eye-popping baby t shirt, carrying a makeup kit. In no time, she had my makeup done, and held up a mirror for me to see. The combination of the tanning, hair color, and makeup, gave me a distinctive Asian look. "A spitting image, if I say so myself. I should get a fucking award," she said aloud, though to herself. I was then dragged into the main suite of our bedroom, and forcefully seated at the computer. Mistress had me lean forward until my face was less than a foot from the screen, then cuffed my hands behind it.

I had no choice but to stare at the screen. "You know, slave, I've been thinking of new ways to train you, and I came across a site you may enjoy." With that, she took the keyboard, and up popped a video. "I thought some videos dedicated to rough sex and female submissiveness would be perfect for you. There's a girl on here named Ava Devine, and I want you to be just like her. Watch and learn. I also want you to repeat what she says as you watch this film. I will be back shortly."

She put a pair of headphones on me and left the room. The video started, and a big-titted Asian (who looked exactly like me) began to speak. "I'm very submissive. I'm a slave to cock. I love men, and I just like to be in their hands. The cock is my master, I'll do anything for cock. I like to gag on cock." This phrase was looped over for the entire thirty minutes of the scene, which involved her calling over two men to toss her around like a rag doll and blast their loads on or in her several times.

They treated like a slut, and fucked her in the most degrading ways, yet the look in her eyes told me she wanted more. The repetition of the video, audio, and just the close proximity to the screen had a hypnotic effect on me, and I found myself repeating the phrases like a wanton slut, and craving some cock in my holes.

I had managed to wiggle my skirt up so that my bare ass was resting on the cold chair, and I was massaging my tits under the sweater, when the door opened and Mistress Brittany entered the room. "I see you're enjoying yourself, slut," she laughed. "You're going to LOVE this," she continued, as she stepped to me. All of a sudden, everything went dark around me. "Don't worry baby, everyone can still see your beautiful brown eyes," she said.

Apparently, she had put in a special kind of contacts that blinded the wearer, but appeared normal to everyone else. "You'll be thanking me for the extra protection, with all the cum you're about to have in your face," Mistress growled in my ear. "I have some guests here, and I want you to show them what you've learned this morning."

With that, I was released from the computer, and stood up to face the rest of the room, where I assumed everyone else was standing. "Hello, gentlemen," I whispered sexily. "I am sure my Mistress told you, I love men and I am very submissive. I am a slave to cock. I love being man handled by rough horny men. Right now, I really need some cock in my holes," I said as I batted my eyes and took off my sweater. "Who wants to fuck me?" I growled as I mauled my own tits over the bra.

I was immediately thrown onto my back onto what felt like an ottoman, two strong hands took my legs and rested them on a pair of broad shoulders and a warm dick plunged into my ass. As I was about to cry out, my mouth was stuffed full of cock. Both invaders began to violently ram me, and I soon had trouble keeping up with the dick in my mouth, as I was on my back and my head was hanging off the end of the ottoman.

Thankfully, I was well versed in sucking cock, and the first one erupted in my mouth in no time. Unfortunately, it carried such a load, that my entire face was covered in cum. Some got in my eyes and hair as well. Cum dribbled down my chin and onto to my still bra-covered tits. For a moment, my ass was empty, and I assumed it was time for them to switch holes. I was dragged to my feet, and I took the opportunity to lean forward, reach behind my back, and sexily remove my bra. I also unzipped my skirt, letting it drop to the floor. Then I bent over at the waist, letting everyone know, I was ready for more.

My hands were placed on two firm thighs, and an enormous cock was jammed into my mouth. Just as I began to gag again, another cock found its way into my ass. It was bigger than the one I had just taken, so I yelped in pain as it stretched me some more. I put one hand on the ottoman for balance, as my assailants began another violent assault on my holes. "Reach back and open your ass," a voice growled, as my hand was removed from the thigh and placed on my ass. I was having trouble balancing on the heels, being bent over and rammed as I was.

I was glad when two hands grabbed my hair and forced the cock deep into my throat, it kept me from falling over. Again, my oral skills proved to be a mixed blessing, as the second cock erupted deep in my throat, spilling yet another load of cum down my face and tits, but buying me some time to concentrate on the dick in my ass.

I was being rammed so hard, that the dick in my ass came out, momentarily leaving me empty. With that, I reached back between my legs, grabbed the cock, jammed it back into my asshole, and took off for the ride. I put my left leg up on the ottoman, and grabbed the back of my ankle with the palm of my hand, looking back lustily at my assailant as I did so. Not satisfied with my performance, I put my leg down, and grabbed both my ankles, bending myself clean in half, and flexing my ass to milk the cock inside of it. It pulled out and erupted all over my back, and down between my ass cheeks. I reached down between my legs and licked some of it off my index finger.

My favorite position is doggystyle. Nothing beats the feeling of having your hair pulled while you're being rammed from behind, so I got down on all fours, and wiggled my ass for my next lover. I was quickly obliged by a cock of medium length, but tremendous girth. I reached up with both hands, and fed another cock into my mouth. I tried to work the shaft with my hands, but I was brutally slapped in the face. "Don't touch my cock, you slut use your mouth only," I heard. I worked both cocks until they erupted, giving me yet another cum bath, but these were ready for a quick round two. A pair of hands guided me into a sitting position, with the cock still lodged firmly in my ass.

"It looks like we have ourselves a little cowgirl. Get riding, bitch, and keep your hands behind your head." I laced my fingers together behind my head, arched my back, and started riding.

"I need more cock for my holes!" I screamed as I bounced. "Please....oh GOD...I'm a cock slave...put it in me...I love cock!" I felt another blast of cum in my eyes that ran down my face, and I was pushed to the floor, dislodging the cock from my ass. My ass was gaping, and I felt the cum trickling into it.

As I was wiping my eyes, and attempting to make another plea for cock, I was maneuvered into the familiar piled river position. A pair of knees held my feet firmly to the floor behind my head, and the owner's cock was jammed into my mouth, making breathing damn near impossible. I got to work on that one, and braced myself for the impending invasion of my ass.

As expected, a dick was fed inch by inch into my ass. It didn't feel very big, but considering what I'd been through, I was not surprised. It felt good, sawing in and out of my ass. I began to squirm and shout, "More....I need more...cock," I mumbled around the one in my mouth. All of a sudden, I felt the worst pain of my life, followed shortly by the most pleasure, as another cock was jammed into my ass. I closed my eyes and tried to envision a big titted Asian in black thigh highs and platforms, thong pulled to the side, being double anal pile driven while taking a third cock in her mouth.

The thought alone made me cum (which was painful behind all the tape), as all three dicks shot their loads simultaneously, flooding my ass, and damn near choking me to death. The dicks were removed from my ass and mouth, but there was still someone sitting on my chest, keeping me immobilized. As I attempted to regain my breath, the person on top of me began to repeatedly slap me in the face with a cock, until the contacts flew out of my eyes. Before I could readjust, my hands were placed on what felt like a large pair of tits.

I looked up to see Mistress Evolin Pierce looking down at me. "Look at how far you've come since the last time," she laughed. "You were begging for it. And you took two in the ass at once? Amazing!" I looked around the room to see all of the Mistresses from the airplane, lounging around the room naked, save for what turned out to be heated, squirting strapons.

I was so confused I didn't know what to do. Mistress Pierce stood up, and the other Mistresses gathered over me as I lay on the ground, a sticky, cum covered mess. "Ok ladies, I think we're ready for the grand finale," Mistress Brittany announced. The Mistresses began stroking their cocks. "One...two...three." As she hit three, the Goddesses all released their loads at once, soaking me one last time, as seven loads hit my hair and eyes, dribbled down my face onto my tits and stomach, and stained my thong and stockings. I writhed on the floor as I massaged my tits and sore, but satisfied ass.

"Thanks for stopping over to play with me," I said as I got to my knees, arching my tits out, placing my hands on my knees and resting my heels on my ass. "A girl can never have too much cock," I added as I batted my eyes and scooped some cum off my tits with my index finger and fed it into my waiting mouth.

Mistress Brittany informed the others that they had all passed day one, with exemplary marks, as she led them to the door. As the door closed, and she came back to me, I began to cry. "What's the matter with you?" she snapped.

"Mistress, I'm so confused," I stammered. "I loved every minute of it...up until the end. I think I was hoping that they were actually men."

"There, there, love," she whispered sympathetically. "We'll 'straighten' this all out in the morning." With that, I passed out from exhaustion, not even bothering to clean myself up, wondering what would happen the rest of the week, and what she meant by "straighten up."

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