Dream Vacation

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.

"Yetthhh Mtthhrsss," I gagged.

"I want you just in your thong, make it happen," she commanded. With a great amount of work, and thrashing, I was left kneeling in just Mistress Brittany's g string thong, sucking her fat strapon cock. It was really hot under the blanket! "You know what, go ahead and put on the heels as well," she said. I have small feet, so that was not a problem.

"I would like some water," I heard her say. I got really still and quiet.

"Would he like anything when he gets back?" the flight attendant asked.

"Water, please," Mistress Brittany replied. I heard the flight attendant leave, and Mistress spoke. "Would you like to see Mistress's titties, slave?"

"YEEETHH Mthrsss!!" I mumbled enthusiastically. I looked up, and she had unzipped her dress in the back and rolled it down to her waist. She wore an exquisite red lace bra that made her magnificent breasts look even bigger! As if in slow motion, she reached back and unhooked the bra, and freed her wonderful knockers.

"Now since you get to see them, you have to wear this," she commented, as she ran the straps up my arms and fastened the hooks behind my back. "That looks so pathetic on you. That bra is made for breasts like mine, big, beautiful breasts," she said as she cupped her boobs in her hands. "Not non-existent sissy boobies like yours," she snarled, squeezing the cups of the bra, and of course coming up with nothing. "Maybe if your a lucky little sissy, mommy will buy you some big bimbo tits and parade you around on a leash. Would you like that?"

"Ythhh Mstrrssss," I replied.

"Of course you would," she said as she stroked my cheek, and continued to pound her cock into my mouth. "I think it's time," she said. "Since you're down there, go ahead and lay the bed down flat for me." I did as I was told. She reached down and pulled me up onto the bed with her, so that we were spooning, but she was the big spoon! I felt her cock, wet with my spit, rub up against my ass, and I knew it was almost time for what I'd been eagerly anticipating for months! She lightly raked her nails down my back, and circled my waist with her arms. It was an odd juxtaposition of sensations, as I felt huge breasts rub against my back and a huge cock rub against my ass!

Mistress slid her cock between my ass cheeks, then paused, and spread my cheeks further with her hands. This was it!! This was the moment I'd been waiting for!! I felt her rubbery cock, wet with my own spit, push slowly, but firmly against my asshole. My ass gave way to inch after inch of Mistress' cock, until she was all the way in. Her hand covered my mouth right as I let out a moan. "You're a dirty boy, aren't you? You're a dirty boy letting your Mistress rape your ass in front of all these people on this plane, aren't you?" she cooed in my ear. I felt her flex her hips, and work her cock like a pro. It felt amazing!

There was a problem, though. The problem was my poor locked cock was in agony, and Mistress Brittany knew it. "You're so turned on with my big cock in your ass, but your poor little cock has to be dying," she said. "I'll give you a choice," she said matter-of-factly. "I can continue to fuck your ass until I'm finished, and give you no release, or I can release you from your cage and give you a hand, but you'll have to clean off my hand. With your tongue."

This was a tough choice! I was so turned on, and my cock was in so sore and crushed, that I needed to be released. Also, Mistress Brittany Andrews had offered me a hand job. That was so much more than I expected. The cost was high, though. I have some odd fantasies (obviously, I'd paid for a week vacation for someone to fuck my ass) but I had NEVER considered licking up my own cum. That seemed really taboo and gross to me.

"Is it such a tough decision, slave?" she mocked me, as she continued to saw in and out of my ass. "I mean, it doesn't matter to me, either way. I just thought I'd be nice and offer. Are you afraid that licking your cum is gay? I'd say that by that logic, me fucking you in the ass is gay, which is ridiculous. Think of how good it'd feel for me to run my nice soft hands....all over your cock....let you blow your load..."

"Mistress, please. Please let me cum. I'll lick it up, I will," I relented.

"You boys are so predictable and weak," she laughed. She removed the key from around her neck and deftly unlocked me from the chastity device. I felt one hand wrap around my rock hard cock, and her other arm wrapped around my neck. "Fuck my hand, fuck my hand while I fuck your ass," she growled. We were locked together, so I couldn't even move. The only movement was her hips pumping her cock repeatedly into my ass. "You like wearing my panties, bra and heels, slave? Does it feel. So. Good. MMM. Take it, bitch! Are you going to cum? Are you going to spill your nasty filth in my hands? Do it. Do it!"

I bit the blanket came harder than I ever had in my life. I closed my eyes for a bit and waited for my body to catch up to what had happened. Mistress Brittany felt that I had taken too long, because I felt her hand leave my cock and soon saw it in front of my face (which was not under the blanket!) I hesitated, and Mistress increased the pressure around my neck and said, "There, now, slave. A promise is a promise. I don't want your filth all over my delicate hands, clean it off now!" Reluctantly, I opened my mouth and felt her dump my load onto my tongue. I gagged, but she closed my mouth and held it closed until I swallowed it. Then she had me lick each of her fingers until they were clean. Once we got through all her fingers, she stuck her index finger back in my mouth, and idly stroked it in and out.

"Such a good slave," Mistress cooed. "How's my baby doing?"

"Oooooooo. uhhhhhh. good Mistress. I'm...exhausted."

"A young man like you? You can't be tired already. Mistress Brittany's cock is still hard, bitch. You're not done." She wrapped her arms around my waist and rolled over onto her back, with her cock still in my ass. Her hands pushed on my shoulder blades until I was in a sitting position. She adjusted my legs so that my feet were on the outsides of her thighs. "Ride my cock, bitch," she snarled. I grabbed the blanket and pulled up around my shoulders so I was covered from the neck down, and began to bounce up and down. My face felt a bit crusty, so I licked my lips to try and get the remnants of my cum off my face. Mistress grabbed hold of my high heel encased feet and began to aggressively thrust into my ass. I was pretty tired, but my hard cock betrayed me. "Shall I give you a hand again?" she inquired. "It will cost you."

"Yes. Yes please Mistress," I panted quietly. I continued to bounce up and down on her cock to the best of my ability, but my legs were starting to shake. The blanket had fallen down, and I was not sure how long it had been that way, I was so lost in bliss. Once I realized it, however, I was mortified, and tried to grab it. "Ah ah ah," Mistress chided me and slapped my hands away. "I'm a bit chilly, so the blanket is for me," she said. She grabbed each corner and pulled it around me so that she was covered, but I was exposed from the waist up. This wouldn't have been so bad, except for the lacy red bra. I tried to lean back, but she laughed, and blocked me. I tried to lean forward and tunnel under the blanket, but I am not very flexible. Then I panicked and tried to get off her cock.

Mistress firmly locked her arms around my thighs. "Oh no no no, baby," she laughed. "I'm in control of this now, you gave that up. I'm going to fuck your ass until I'm good and ready to be done with it," she informed me. My panic had caused my erection to disappear completely, and of course Mistress knew it, and exploited it. "But I'll make you a deal. I'll stop once you cum again," she promised. "You fill my hand with your filth, and I will stop raping your ass." That was all the motivation I needed, and I began to grind my ass up and down and back and forth on her cock with renewed vigor. I found that the grinding back and forth stimulated me more, so I did that. Mistress slowly rocked her hips back and forth as well. What a pro!

"Thank you...thank you Mistress." I whispered.

"Oh you're welcome. What a good cognizant slave. That's very impressive!" she complimented me. She latched onto my bra strap and began to thrust a bit harder. "You're not just a pathetic sissy in panties, bra and heels, getting ass raped in public by goddess, you actually have a brain. That makes ME a bit horny," she cooed. "Do you like making me horny?" she asked.

"Mmmmm, uhhhh,"I replied. We could both tell I was getting close. She was truly an expert at male manipulation! "Mmmmfff...mmmffhhh...Mffffffhhh!!" I grunted, sprayed into her hand and slumped forward as far as I could. Mistress wiggled her hips a few times to remind me (as if I'd forgotten) that she was still inside my ass. I heard a noise, and looked back over my shoulder to see that she'd adjusted the bed to a 45 degree angle with her clean hand. She wrapped her right leg around my waist and locked her right foot under her left knee.