My palms were sweaty, my stomach was growling, and my cock was twitching. All of this was expected, especially the stomach as I hadn’t eaten anything substantial in fifteen hours. I was trying to keep things clear. This was not the first time I would be a willing anal bottom, but it was my first with a woman; a woman I had worshipped for three months now.
The flight into Liverpool was a little rough over the ocean but once I landed things went as smoothly as possible. The trip to Hotel Chester, a lovely Old-World affair was filed with new sights sounds and smells. at least new to me. I was born and raised in the Midwest of the states, and this would be my first visit to anywhere in Europe.
I stood in my third-floor hotel room watching the cars and busses outside, the smell of the sea wafting through the open window. In the past I would have marveled at of it all but today…today I had one thing on my mind: being ready for Mistress Ana. My ass – no, my boi pussy was clean and lubed, and my dick was hard and snugly sitting in the pouch of my new panties, or knickers, as Mistress called them.
I “met” her online in a chat on the Lush Stories site. In the months since joining, I had discovered a new breadth to my sexuality I did not know I had, let alone craved. A new revelation was a desire to be with a trans woman. I am a confirmed bisexual and have enjoyed cock, ass, and pussy in a variety of shapes, ages, and persuasions. Meeting Ana showed me I had more to experience. I admit that in my limited life, the only trans women I had seen were in porn. Mostly women with fake tits and average cocks. It was an interesting world that never really “took me there.” So, when I first saw her in my Matches list, I was hesitant. When I read her profile, I was intrigued. When I saw her media, I was hooked. When we chatted, I was hers.
The first few messages were perfunctory hellos and what-do-you-likes. She asked if I had read her profile and did I know she was trans. I said yes, and she asked if I read that she liked to be a Dom and I said yes.
I guess it was the right thing to say because my messages were suddenly flooded with GIF after GIF of hot trans women! Most were jacking off and cumming with gorgeous, thick dicks. Some were being sucked by male bottoms and some were being anally fucked and hard! And the last third, were doing the fucking. Something switched in me. I have had a nice cock in me and liked to do the same for few partners. But this before me, the proverbial best of both worlds, was mind-blowing. I had to have more. She gave it with the last picture—her stunning self.
Fast forward past thousands of media, stories, and better porn and I was finally ready to take the plunge. Mistress Ana, as I now called her, said, “The only way you will ever truly know yourself is if I show him to you.” Fuck me, that was it.
This morning, my orders are simple: be clean be ready be willing. Well, I was all three, along with a heavy dose of afraid. What if, after all this, she rejected me?
It was now ten minutes past when she said she would arrive. I checked my phone and suddenly a message popped up!
“Look out the window.” The window? I was just –
Standing across the street on the sidewalk was a vision in black and red. There she was, staring at me from 30 meters away. She had on tall black heels and stockings. Her short, red dress hinted at the top of black thigh highs. The neckline was not enough to hold her exceptional bounty. Her breasts pushed through the fabric, and even from this distance, I could tell was not wearing a bra. Her face and hair were just the right amount of elegant glam, and she was smiling.
But the best part of her entire appearance was what she was carrying. It was a riding crop and it had my name on it. I wanted it, oh yes, most definitely. With my jaw hanging down, I watched as she made away across the street. If I wasn’t so excited, I would have jumped out the window and ran to her. But I knew better than to disobey. She said to wait here, and I was going to follow orders. Five short minutes- no, five agonizing minutes later there was a knock on the door. Wearing only the blue panties, I knelt as instructed, eyes on the floor, and said softly, “It’s open.”
The door opened and closed and soon before me were the black heels I had seen through the window. I also knew better than to look up, even though I desperately wanted to. A Fantastic tenor voice chuckled softly. ” Hello, Matt Pet. You may look at me.” And I did. She was a vision of heat and sex. A red and black gift wrapped in skintight perfection. Her makeup and hair were stunning and her red lips plump and powerful. They smiled as I shivered in anticipation.
“I am pleased that you had made this journey. You have honored me thus far.” She turned away and I saw she had a leather woman’s carryall. Oh my, what wondrous treasures might be in there?
Mistress Ana, gorgeous Mistress Ana, was more stunning than I ever imagined a regular guy would be with. Especially me. I have never imagined myself to be on my knees for anyone. I felt like I was in the right place doing the right thing. I decided I would take a chance.
“Oh, my God Mistress, you are so beautiful!”
That risk proved to be a life changing. Mistress turned around, and her hand was the same riding crop I saw through the window. My voice choked for a moment. My eyes looked like an animal caught in a hunter’s scope. She smiled, and it looked wicked and wonderful. She took the crop, gently slapped the bed right next to her. The sound made my heart skip a beat and my growing cock tighten my panties even more.
“On the bed, Pet. NOW!”
It was like a spring was released inside me. I leapt up to the bed knowing to get on all fours. Mistress had told me this was how she loved to apply punishment. The first weapon was not painful. She ran it up the back of my naked thigh, and across my panty-covered ass cheek. It felt like she was tickling my flesh while taking inventory. She ran it down the crack of my butt, and I shook from head to toe, every inch of me on fire. She ran it up my back and stung my shoulder.
“You will speak only when I allow it. I would hope you would have understood the simplest of rules, my pet.”
The swish in the air was unmistakable. The crack against the back of my leg, this first painful contact from my beautiful mistress was like nothing I’ve ever experienced. I did not care that it was painful. In fact, I embraced it. What excited me most was its origin. I grunted and held my breath to hide my reaction. The second one on my other leg was harder but equally exhilarating.
“This is what happens when my pets disobey.” Slap! Slap! Slap! A total of three on each thigh. Eight smacks of heaven thus far.
Tears began to form in my eyes, but I held back. A dark spot began to form on the front of my knickers. My cock began to drip with eager anticipation of what was to come next. Mistress ran her own fingernails up the back of my leg, and I almost fell over with the power of her touch. Small electrical threads connected us. She rubbed my ass cheek and ran her finger down my crack. I thought, ‘Please, take them off!’ and like magic, she did. The garment slid down to my knees, and she left it so they would stay close together. Mistress’ warm red colored fingers reached up and spread the cheeks of my ass. Mistress could see that I had followed orders, and a pink jeweled butt plug shown in the light of the room.
“All this pleases me Pet. What a lovely choice and a lovely color. This will help us both later.” A slender digit slid up and circled the jewel in my ass. She twisted the plug clockwise, and I nearly shot a load onto the duvet.
“Ohhh….” I moaned out, elated to have her finally touching me in the way I had dreamed about. She took the plug and pulled gently, and it started to slip out of me! Halfway out I started to breathe in pants! Then she shoved it back in! That gesture was followed by a hand slap against my right cheek echoing like a gunshot in the room I am sure the neighbors would hear! I cried out and she hit my left cheek so they would match. Ten…
I was hoping it would continue, but Mistress had something else in mind. She was suddenly in front of me on the bed.
“This day is for you and me. But never forget all of your pleasure will come at my discretion.”
She lifted her red dress and something stupendous sprung forth. Something I had seen in the photographs she had blessed me with. Something I had dreamed about morning and night and had woken me up in the wee hours. Mistress’ majestic member stared me in the face. It’s brown and purple color, a slight shine of moisture. Ball below on site. My mouth watered immediately looking at them. I did want to suck it for hours. I wanted to lick those balls just as equally. Mistress saw my fascination and her smile told me it was just what she wanted. She continued raising the dress and soon it was lying on the pillow next to her. A gorgeous, black with red lace trim bra was revealed, holding her EE breasts. Her light brown skin was smooth and inviting on her whole body, but the tops of her glorious tits were calling my name. Her voice called me back.
“Prepare me.” It was a phrase I had waited so long to hear that I actually froze for a moment. It was a mistake as the crop swung over my back and collided just above my ass cheek. Another loud slap was hard as it swung down, and hit again in the same exact spot. Twelve…
I was shaking in lust and pain, my mouth open with desire. I extended my tongue and Mistress push herself forward. Her head made contact with me for the first time, and I almost had an orgasm right then. The taste was magical, like potion was dripping on me from some other world. I had tasted pre-cum of a few partners and of course of my own making, but this was another recipe Nature shared with select diners. I swirled around the head and sucked it in gently with my lips. Mistress moaned softly, and I was delighted to be pleasing her. I attempted to get more inside, and she pushed forward. Three magical throbbing inches entered my mouth. I used as much tongue as I could to make the slide even, though I felt slightly dry from all the anticipation and some fear. Not of the pain she was causing, but blooming from my own inadequacy in pleasing her. I must fail her now. My mouth began to move up and down my tongue swirling around this unique piece of woman in front of me. Then she did something I never expected. Then again, this was all unexpected. She laced her fingers through my hair and pulled. A small amount of pain was delivered by a truck full of excitement.
Mistress was fucking my face, thrusting her cock to the back of my throat. She pulled out until the tip was on my lips. Then she pushed back in, hard thrust after hard thrust. I was absolutely dumbfounded how much pleasure I was getting. I was thankful that she had removed my panties because I’m sure they would have been ruined by now.
After a dozen or so more plunges, she pulled out, and I whimpered disappointment. The fingers in my hair pulled my head up until I was looking at her sumptuous bust. She put my face between, and I smelled perfume that intoxicated. The taste of our precum in my mouth. My lips began to work up and down her cleavage. How did I get so lucky to have this creature as my dominatrix?
I ran my tongue up the edges of her bra and back down the other side. I was moving my mouth in any way I could to give her pleasure. I even took the risk of nibbling slightly with my teeth, and she pulled my hair tightly to let me know that was not allowed. I moaned softly into her flesh, “I am sorry, Mistress.” I recognized the error of speaking a second later, when that delightful weapon of sexual adventure collided with my ass cheek again with four loud slaps. This time, I did not even flinch. The pain was encompassing my entire lower region. And I wanted more. Sixteen…
My head dropped with the painful recovery. There before me was the wand of destiny, still wet with my ministrations. I had almost forgotten the curvaceous bone that soon occupied my entire mouth. But Mistress had not. Her thrusting actually increased in power, and I was beginning to feel the gag that she had warned me about. Her cock felt so right in my mouth. Saliva began to expel out my lips and drop the bed. I did not care. It was if I was christening her with the fluid of my devotion.
I began to revel in depth at this debauchery when suddenly the grip in my hair increased, and she ripped my mouth off of her. I gasped in both disappointment and shock. I was shocked when she tossed me easily to her left, and I landed on the bed on my back. I flinched at the contact because of all of the torture she had blessed me with. My skin was alive and wanting. My unworthy cock bounced up and down as I landed. Mistress did not hesitate for a moment, and the crop of devotion sailed through the air again and delivered for quick blows on my thigh, dangerously close to my balls. Eighteen…
These actually hurt worse than the ones on my ass, and I could not help but reach out to protect myself. My fingers soon received the same punishment, and I withdrew them immediately. Nineteen!
Mistress positioned herself between my legs, and I instinctively knew what was coming. I lifted my knees to spread my boy pussy for her, but was encumbered by my silk knickers. She chuckled softly.
“Good Pet. Are you ready to receive me?”
It seemed a silly question. I had never been more ready for anything in my entire adult life. In all of my forty years of sexual encounters, my body had never been more prepared, or aroused, or more unworthy of anything. Mistress reached out and her red fingernails gripped my panties and tore them.
When she pulled the plug from my hole it felt good and bad, and I loved it. She lifted it toward my face, and I opened my mouth. She slid it in. I instinctively closed my lips around it. I was thankful I had cleaned myself out with edible lotions. It was not a bad combination of flavors, just slightly sour.
“Hold it in your mouth until I say otherwise!”
I nodded as Mistress lined up her gorgeous cock with the opening of my pussy. This was it. The moment I had dreamed about. The moment that above any so far today was the one I had most often re-worked in my fantasies. But nothing matched reality.
I looked up at this Venus smiling down, her lips showing a small number of teeth. Her eyes glistened with lust and just a little bit of evil. But what also caught my eye was that her gorgeous nipples were not exposed. She had pulled down the front of her bra and they listed just above the lace. They were brown and round and protruding and pink and delectable, and I wanted them badly. Because she is so wise, she sensed my desire. She reached out and took my left hand in hers and brought it up to her right breast. I shook nearly to orgasm as my hand was allowed to rub across her distended nipple. She closed her eyes and smiled softly. I must be doing it correctly. My fingers were soon closed around her nipple, and I rubbed it, slightly pinching. I began to pull it out away from her body when she slapped me, and I dropped it quickly.
“Do not presume, Pet!”
I mumbled around the butt plug still in my mouth. ” I um thorry, Mithreth.”
“Despite that infraction, I am still going to grant you the reward that brought you all the way across the ocean.” She grabbed my chin and held my frenzied gaze. ” What I am about to give you only a few have been deemed worthy of receiving. Do not mistake, even though you have traveled far if you displease me, this is the only time this will ever happen. Keep that in mind while I fuck your unworthy pussy. “
And with that, she pushed me back flat, and I was sent to another plane of existence.
She did not enter me slowly, or with affection, nor with even the slightest sense of giving me pleasure. It was a hard, aggressive thrust of the most magnificent fat eight inches of cock I had ever seen. She thrust of her length into me and then froze. I screamed out in pain! I had never had anything so large. The plug rolled out of my mouth and landed on my chest. Mistress did not tell me to pick it up, so I left it there. My breath was coming in sharp pants as I tried to control the pain. My legs were shaking and trembling, a combination of sensations I never imagined.
Just as quickly as she had entered, she pulled out. I felt relief and frustration. The fuck was repeated. This time, even more of her tube entered me. I was being split in two and I wanted nothing more than to encourage it. Another withdrawal and another entry soon commenced a strong rhythm and momentum. I instinctively put my hands behind my knees and pulled both my legs up even closer to my shoulders. This allowed mistress even more access, and she was finally all the way inside me! The thrusts were now deliberate and steady, and her smooth balls slapped against my ass cheeks.
My own pathetic cock bounced against my belly. It dripped with the promise of exploding soon. And even though she had not said so, I knew better than to cum without permission. The wait would be agonizingly more difficult in the next few moments. Her body was now over me and her hips kept thrusting. Her hands were just under my armpits, supporting her curvaceousness.
Amazing breasts swung back-and-forth and side-to-side right in front of my face, my tongue watering with each pass. I really wanted one of them in my mouth. And again, as if she were a mind reader, Mistress saw. She paused her thrusting and grabbed the back of my head. Instinctively, I suckled the most glorious breast I ever experienced. The nipple was soft and bumpy and hot! It felt perfect in my lips. She squeezed the back of my head, pulling my hair again and I knew to go harder.
“Suck me harder! Harder! Do not bite! I want to feel your devotion through your lips, only! Suck me harder!”
I was doing as much as I could with the stress of my body being compressed upwards. I knew this was part of giving myself to her. The strain on my neck and back showing my devotion to this woman was all that mattered. She returned to thrusting even harder as my nipple sucking became more aggressive. She pulled me off and directed my mouth to the other side. Without hesitation, another incredible seat was met with craven lust.
I felt her sweat raining down onto my body. Her bra was starting to darken with moisture of our shared passion. Her energy drove her closer to glorious climax. Her balls against my ass rhythmic accompaniment to the praise song I was singing in my head. “Praise God from whom all blessings flow!”
Mistress reared back, and my mouth naturally fell away. My body slammed back into the mattress. She grabbed hold of my knees again and pushed up even further. I was nearly bent in half, my ass and lower back now actually off the bed. Her thrusting was like a machine of lust and, dare I say, love. Her face was gleaming with sweat, but she was still the most gorgeous creature I had ever seen. This woman was blessing me with something that was life-changing, and I was going to receive all of its never-ending delight.
Mistress stiffened and drove in with one more thrust!
Explosion!
The inside of my body was electrified by a feeling that I can only describe as otherworldly. The amount of cum she was injecting inside of my ass was unimaginable. My own cock was moments away from expelling, and I was shaking trying to control it. In the midst of her fantastic orgasm, she took pity on me and reached between us to grab my inadequate dick. The contact was all that was necessary, and I was soon pumping my own blast all over my stomach and face. My mouth was open in a scream of pure sexual collusion! Several shots of my own orgasm landed in my mouth.
After what felt like ten minutes and was probably closer to two, my body started to relax back to the bed. We remained en-coupled, her throbbing inside of my throbbing. We were made for each other. Sexual euphoria informed me my life was starting right now. This is where my body belonged: underneath, wanting, hosting. Unworthy, yet blessed.
As my aching legs stretched out around her body, I felt the weight of her on me for the first time. Her nipples rested hard against my own chest, and her mouth was panting in breath, just inches away from my own. Would she bless me with the ultimate gift? I dared to look her in the eyes and saw lust and satisfaction. But the traces of evil had disappeared.
I got my final wish. Our lips were soft and wet and hot. Mine felt small and unworthy, yet we met with such beautiful grace and passion, that I never wanted to cease kissing. She even gave me her tongue, and I sucked on it with sheer devotion that I had shown throughout the entire fantastic encounter. Once she was satisfied, she pulled away and left me wanting more. I made another error by whispering, “please…!”
Without moving much, her left hand hit the back of my thigh with three sharp blows. I was now embracing the pain, even craving it. Twenty-one..
She saw the look of confused pleasure on my face. “You may thank me.”
I opened my eyes and whispered through a blissful smile. “thank you…Mistressss.”
“This was the first of what I hope will be many of these, My Pet. But know this: I rarely give away my mouth to those who serve me. Your pussy was quite satisfying, and I felt compelled. If you ever tell anyone I will not only cut you off my from body, I will actually cut off your balls from your own.”
My eyes must’ve been the size of saucers, because she laughed a thready evil laugh. “Priceless! I would never do such a horrible thing, but seeing your reaction shows me just how much fun you are going to be in the future, Matt, my pet.” To remind me of the promise, she pulled back and slapped my scrotum, and I arched in pain. Twenty-two…
Mistress’ shrinking cock was sliding out of my hole. Cum was running out down my cheeks, and I’m sure it was making a puddle on the duvet. I looked down and saw her love tool glistening and dripping, and I wanted it badly. Mistress snapped her fingers and pointed at it, and I manipulated my body around until I was underneath her, still on my back. Her thigh-high stockings felt wonderful in my bold hands. She did not remove them, and I sighed in gratitude.
My tongue and lips took her in again, and she slowly thrust in and out with her wilting bone. I sucked in every drop! I could even taste the lube and my own dirty musk on it. It was the most fantastic thing I’ve ever tasted. Mistress had reached down and scooped up some of my own cum off my stomach. She dripped my cum into my mouth, and I willingly took it all in.
“You may swallow.” I made a display of gulping and then opened my mouth to show it to be empty. I had dodged a bullet, because I know that she knew I had already swallowed much of it without permission. And she was willing to let it go.
She was clean to her satisfaction and climbed off of the bed. I lay there, waiting for orders of what to do next. I surveyed my body and discovered the pain I didn’t know had been afflicted. As her glorious ass walked away from me toward the bathroom, I could not help but wonder if I would ever get to worship it with my mouth. I heard mistress emptying her bladder into the toilet. I longed for that as well. So many changes had come over me and just a short – I looked at the clock, half an hour, since she had walked in. Half an hour that in this other dimension of sexual bliss seemed like a day! I closed my eyes and breathed in all of the smells and pain on my tortured body. I had not noticed that she had climbed back onto the bed and was sitting next to me. I saw her, Ana, smiling at me. I say this because I think, mistress disappeared for a moment.
“Well, I have to tell you that was one of the best first encounters I ever experience. You have a lovely arsehole. I am keen on exploring for the next couple of days. Did I meet your expectations? Speak freely. We are no longer in our relationship. This is just Matt talking to Anna.”
“It was… Indescribable. I honestly feel completely different. It’s like my old self was left on the plane at the airport.” She smiled again. “And I never want to see him again.”
She ran her hands through her hair and chuckled with that beautiful tenor British voice. “Well, that was poetic. I guess you cannot abandon the writer in you, can you? But you have given up your old sexual self. I sensed it. Not just in your words, but in your body.” She leaned forward and kissed me softly. “Well love, I’m glad he’s GONE.”
That she yelled at me! Her hand grabbed my hair and pulled me up into a sitting position. Our arms were twined together, and we kissed like lovers have done for thousands of years. I was lost in a feeling of lust that I let encompass me in warmth and satisfaction. I didn’t care about her fingernails scraping across the welts and bruises she had given me. I didn’t care that my asshole was making a mess underneath me because it was her glorious cum that was doing it. I didn’t care when she pulled my tongue, and I flinched in pain because it was with her teeth. There was nothing but her, the room, and this new me.
“I like to do things in tens.”
I sat confused. She made a spin motion with her finger. I willingly turned around and offered my sore ass.
“Four on each should make the set!” The crop was magically back in her hands and the swish was an aphrodisiac. My pathetic cock swelled as the Thwack! of impact took my breath.
Twenty-two, twenty-three, twenty-four…