Preface: For as long as I can remember, I've wanted to have an experience with a dominatrix. Not just a session, but an intense experience. Recently, I've come upon the money and a life situation that would allow me to do this. There are many Mistresses with whom I'd love to share this experience. Mistress Nikki Whiplash, Mistress Alexia Jordon, Mistress Evolin Pierce, and Mistress Tangent would all be wonderful. The perfect Mistress, though, is the only Mistress I've loved for the last fifteen years, and that is Mistress Brittany Andrews. She is simply gorgeous, in all ways. She is a great mixture of elegant and classy, and downright kinky and filthy. Here is the letter I wrote to her:
Dear Mistress Brittany
I am a thirty year old, professional man. I would like to offer to take you to England with me. During this week, everything would be on me, anything you want. In private, and public, I would do as you command. I can be a well-dressed, classy, gentlemanly companion, or a completely feminized sissy slut. That is up to you, Mistress Brittany. My only request that at some point on the tran-Atlantic flight that you take my pathetic sissy ass with your magnificent strapon girl cock. Upon meeting at the airport, I will hand you the key to my chastity device and my credit card. Any images and/or videos you take of the experience are yours. I will sign away my rights to them, and you may sell them or humiliate me with them in any way you see fit.
Humbly yours,
K
What started out as the above detailed trip, has turned into something else altogether. Here is what happened:
It has taken me awhile to write down my life-altering vacation with one Mistress Brittany Andrews. Each time I try and sit down to write, my mind wanders back to the experience, and I get lost in bliss and am unable to write it down. I shall attempt again, from the beginning.
To my utter shock Mistress Brittany did respond to my letter, and agreed, in principle, to my idea! Of course, we had tons of correspondence back and forth, to iron out the details. She wanted pictures of me, shaved from the neck down, and wearing only a pink g string in three poses: kneeling, bent at the waist (side view), and ass. I complied immediately. She also sent me legal releases for me to sign, so that she could in fact, use my likeness and image in any photos/videos without further compensation to me. I inquired as to which sex toys I was to bring, as I was not sure if Mistress wanted to go through security with any of them. Mistress Brittany responded that she is very particular about her harnesses and cocks, and would be bringing them with her. I was told that the only thing I had to worry about was that my cock was locked in chastity when we met.
My in-flight dress was to be a suit and tie (which was a bit of a bummer, I did not really want to wear a suit on the plane). Mistress also asked me about my experience (which I admitted was none). She seemed a bit hesitant at first, but then became turned on by the prospect of "breaking in a nice young man and raping his ass." At her request, I sent a picture of my ass wrapped around four inches of dildo, and she responded with a picture of her cock, which she told me was six inches. I immediately got to work training my ass to take more.
After a few months, it was finally time! We were to meet at the airport in New York and fly to England! I barely slept the night before, and definitely rubbed out several in anticipation of meeting my Goddess. (Also in anticipation of not knowing the next time I'd get release). Once I was thoroughly exhausted, I locked my cock into its chastity device, put on my suit, and headed to the airport. Mistress Brittany stood in waiting area, a vision of radiant beauty that I cannot fully describe. She wore a curve-hugging red dress that ended about two inches above her knees. It had quarter sleeves, and a low neckline, which showed a tasteful amount of cleavage. Four inch red pumps, earrings, and a necklace completed her outfit.
Mistress recognized me from the pictures, and strode confidently over to me. She embraced me as though we were long lost friends (or lovers!), but whispered in my ear "I hope you're ready to be owned, young man."
My voice caught in my throat, but I was able to whisper back, "Yes ma'am." She turned on her heel, and headed toward the plane. I struggled to grab both her carry-ons, in addition to my own but I managed to get it all on board and stowed. We were up in first class, with the flat bed seats, which were very nice! We talked for a long while, about my life, about her life, her career, her travels. There were not many people around us, since we had the flat bed seats, we all had plenty of space, but there were people in the area. It started to get dark, and casually handed me an iPad and hit 'play.' I immediately recognized it as one of her magnificent strapon movies! It was the one where she enters the room in full domme leathers to her sissy maid cleaning her cocks.
I winced in pain as my erection was squashed in its cage. To add insult to injury, she smiled cruelly and subtly rubbed her hand over my crotch a few times. "What's the matter, little boy?" she purred. "Is your poor little cock stuck? We're just getting started," she laughed. In her hand, was a good sized black butt plug! Quickly, I took it before anyone could see it. "Go to the bathroom, and come back with that in your slut hole," she said. Obviously I knew this was going to happen, it's what I'd wanted my whole life, but when it came right down to it, it was very difficult. It was also the reason why I didn't want to wear a suit on the plane. What a hassle! She shifted her weight a bit, and right as I turned to walk away, she handed me her red g string thong and said, "You'll need these to hold that in," she winked. I wadded them up in my fist, and hurried over to the bathroom.
As everyone is aware, airplane bathrooms are tight spaces. I sat down on the closed seat, and removed my shoes, pants and boxer briefs. My poor throbbing cock was in agony down there, but there was nothing I could do to help him. The butt plug loomed large in my hands. It was actually a decent size, and certainly one I could handle, but I didn't have any lube! For a split second, I considered using the hand soap, but I had no idea what would happen, and didn't really want any kind of problems since we were in the middle of the ocean! All I could do was part my lips and stick the butt plug in my mouth. I got as much spit on it as possible, Once I felt it was as good as it was going to get, I stood up in a squat and set the plug down on the closed toilet seat. My hands parted my ass cheeks, and I slowly lowered myself onto the invader. Initially, my ass did not want to give way. I gritted my teeth, spread my cheeks further, and pushed down harder onto the plug until the tip slid past my sphincter. I bit my wrist and continued to push down, until the plug was buried all the way up my ass.
Then I heard a knock at the door.
"Sorry," I panted. "I'm almost done," I said.
"Are you ok in there, you sound distressed," she said.
"No...no, I'm fine!" I assured her. (I thought to myself, "Holy hell, what noises did I make?) I put the g string to my nose and inhaled Mistress Brittany's divine scent, and then I slid it up my legs and settled it into my ass. I bit my arm again to stifle the moan, because the silky material teased my poor cock even more. I put on my pants and shoes.
There was another knock at the door. "Sir, I am a flight attendant," said the voice. "If you don't come out, I'm coming in!" At that, I stashed my underwear in the trash (I had nowhere else to put them!) and opened the door. She ushered me back to my seat,
"Oh I'm glad you're ok!" Mistress Brittany smiled. "Thank you for checking on him" she said to the flight attendant. My face burned red and we headed back to our seats. "I was just reliving some of my better on-film moments in ass-raping," she told me, as she handed me the iPad again. On screen, Mistress Brittany was in her dungeon had a slave bound over a sawhorse and was fucking him in the ass. The combination of the g string, butt plug, and cock cage was almost too much for me. I was in so much pain, and Mistress just raked her nails lightly down my cheek and breathed on my neck. "I just love torturing my little pets," she purred. I closed my eyes and tried to think of anything else, but it didn't work. She grabbed my chin and looked me in the eyes. "Do not run from this, baby," she said, as she turned my head back to the movie.
"My feet are tired, rub them for me like a good boy," she said. I carefully took off each of her heels, and began to rub her feet. After a bit, she said, "It's kind of cold in here." I immediately looked at her tits. "You men are all the same," she laughed, as she threw a blanket over both of us. "You know, watching this makes me kind of horny," she purred in my ear. She took my hand and put it between her legs. Obviously, when I'd been in the bathroom, she'd been getting ready as well, because I felt my hand brush up against her strapon cock. "Why don't you give my girl cock a loving hand?" she inquired. "Stroke it how you'd want to be stroked...you know...if you weren't all locked up," she added. With that, I began to slowly stroke her cock under the blanket. "Ohhh, that feels good baby," she said. "You're making me so hard, I can't stand it. Take off your shirt and tie," she commanded. I began to loosen my tie, and she interrupted me. "You can't get me going and then stop," she said. "If your hands are too busy for my cock, you're going to need to find another way to attend to it."
This left my mouth or my ass, and at this point, it had to be my mouth. "On your knees, slave," Mistress Brittany growled. Carefully, I knelt down on the floor directly in front of her and adjusted the blanket so that it covered all of me, and covered her from the neck down. I reached up and removed my necktie and tossed it to the ground. Mistress Brittany moved her hips and worked her dress up, so I could lean forward and engulf her girl cock with my mouth. It was very rubbery, and I accidently went too far too fast, and gagged. She slapped me, and I got my problem corrected, and soon got into a good rhythm.
At that point, I was able to continue unbuttoning my shirt, and tossed that on the ground as well. Mistress ran her fingers through my hair, and guided my head up and down on her cock at a speed and depth that suited her. "That's a good little bitch," Mistress whispered. "You better do a good job getting Mistress's cock ready, because you're about to become my mile high princess," she promised. "My girl cock is going up your ass," she said.
