They say that the perfect match is made of two switches. I would concur. When I met Moira, it was the best day of my life, at least until then. Subsequent days have brought blissful experiences that exceed anything I could have dreamed. She and I are extreme switches who both love the giving and receiving of severe sexual pain. Occasionally, we will crave the same side of the coin simultaneously, but we worked out a simple solution for that conundrum long ago.
Using social media, we found several playmates who were happy to explore our submissive and dominant urges as a couple. Moira was always bi and open to playing with women in either role. I required a bit of convincing to play with men, and admittedly I still prefer transgender women when it comes to cocks. Conveniently that turns Moira on immensely, and on a coupled of occasions when she has been in Domme mode, she has cuckolded me with cismen. I can’t say I liked it, but my cock told a different story as the humiliation seemed to be a source of arousal.
This weekend we have planned a different adventure. A local group is sponsoring a retreat at a unique resort located deep in the nearby woods. The resort caters to kink and features special facilities geared to intense BDSM experiences for the guests. We have been craving submission this week and will be going to the retreat as solo submissives. When the weekend is over, we will return to our wonderful life together, but we will be on our own this weekend.
When we discussed our plans for the adventure, We were hoping to encounter new dominants who might take us to new heights of delicious submission. Moira suggested that I might find the unicorn she knew I craved, a beautiful transgender Dominatrix who would train me in skills I had been struggling with. It was a selfish wish on her part. She loved watching me suck cock, something I found difficult to embrace. I wanted to please her, so I was determined to seek out this sort of adventure.
For her part, she had agreed to seek a match with a sadistic bi couple who could take us to new heights in an ongoing relationship. Moira loves genital torture and receiving deep fisting. I adore that about her. I have fisted her in both holes many times and delight in watching the transcendental state it engenders for her. I say she agreed to, but I must say her eyes lit up in expectation when I mentioned it.
We parted ways in the parking lot and proceeded to the registration desk separately. A severe-looking middle-aged woman, obviously Domme, checked me out while she checked me in.
“What sort of fun are you looking for? You’re a sub, aren’t you?”
“Yes, and I would love to get better acquainted another time, Ma’am, but this weekend I am looking for a specific adventure.”
“Mmm, that’s intriguing. What sort of partner are you seeking?”
“I hope to find a transwoman Domme. If she’s tall and beautiful, it would be a plus.”
“You may be in luck. A lovely woman checked in about half an hour ago who sounds like a match. She said she was heading for the bar. Just follow the path until you come to the main building. Her name is…” She thumbed through a pile of cards, “Cassandra. Tell her I thought you might be what she was looking for. I know you will find her interesting.”
“Thank you so much, Ma’am.”
“I look forward to seeing you again, Max.”
“That would be wonderful, Ma’am.”
“You have no idea. Now go and enjoy Cassandra. She has long red hair and is wearing a black dress.”
I hurried along the path to the large log building that I assumed housed the bar where I would find Cassandra. There was no mistaking her when I walked in. Her presence was regal as she sat in a booth along the far wall. To say her hair was red was an understatement. It was the richest dark red I had ever seen. Long and curly, it trailed down past her shoulders and onto her large breasts that strained to escape from the black dress. She wore thigh-high boots. Her legs were crossed appealingly, and she sipped champagne from a flute.
Shyness has never been a particular problem for me, so I approached her confidently.
“Hello, Miss Cassandra.”
“Do I know you?”
“Not yet.”
She chuckled a lovely, throaty alto and granted me an inquiring smile.
“The Lady who checked me in suggested that I look you up.”
“Oh?” She looked me up and down appraisingly.
“Yes, Ma’am. She told me that she thought we might share similar interests for the weekend.”
“What interests would those be?”
“She asked what I was seeking at the retreat. I told her that I hoped to meet a tall, beautiful transwoman Domme. You certainly are beautiful.”
“Thank you. Have you had experience with transwomen?”
“A couple of times, Ma’am.”
“Did you enjoy the experience?”
“Mmm, yes.”
“That wasn’t very enthusiastic.”
“I’m new to this, and they weren’t gorgeous like you.”
“You are submissive.” It wasn’t a question.
“Oh yes, Ma’am.”
“Call me Miss. I don’t like Ma’am.”
“Yes, Miss.”
“Are you an experienced subby boy?”
“Yes, Miss.”
“I like the looks of you. Would you like to see where this takes us?”
“Yes, please, Miss. I would like that very much.”
“Good,” She rose and breezed toward the entryway. I followed eagerly as she led me to an elevator. When the elevator arrived, she entered, and I followed eagerly. In her spike-heeled boots, she towered over me. She was tall and beautiful as I had hoped for when we arranged for the retreat. My cock pushed against my zipper, hardening already.
We were alone in the elevator. She pressed the button for 4, let the lift rise partway, then pushed the stop button. Stepping close to me, she grabbed me through my pants. My cock was already stiffening with anticipation, and she smiled wickedly.
“Good, I like my subs to have a substantial cock. I think you may be worth the effort.”
“Thank you, Miss. I hope I please you.”
“I’m sure you will.” She pressed the button, and the elevator resumed its trip.
As soon as we were in her room, she instructed me to strip and had me kneel in the center of the room. She strolled around me, inspecting.
“What are your limits?”
“No scat or permanent damage.”
“Excellent, scat is gross, and good you’re not insane.”
“Thank you, Miss.”
“I will let you have a safe word.”
“Red light?”
“Very good.”
She strode over to a wall closet, where she took out an oversized leather duffel and laid it on the end of the four-poster bed. In keeping with the resort’s theme, each of the posts had a leather shackle attached. She opened the duffel and withdrew a black leather flogger. The tresses were thick and severe-looking. She drew them across her palm and looked deep into my eyes.
“Is that fear or lust I see in your eyes, slut?”
“A little of both, I think, Miss.”
“Perfect.”
She trailed the tresses over my shoulders, first one, then the other, letting the ends tickle my nipples.
“I like my subjects to offer themselves unbound at first. Your desire for what we do should be sufficient to restrain you.”
“Yes, Mistress.”
She nodded and reached into the duffel. She produced a good-sized butt plug and a tube of something. As she came closer, I recognized the writing on the tube. Ben Gay. I knew what she planned to use it for. She squirted a large glob of the liniment into her palm a slathered it onto the plug. She directed me into positioned with a flick of her fingers.
“Bend over and open yourself.”
I obliged wordlessly, knowing full well how much this would hurt. The smell of menthol was overwhelming. She stepped behind me and brought the tip of the plug to my anal opening, grabbed my hip, and thrust it into my has forcefully. I gasped at the intrusion. There was pain, but nothing I wasn’t used to. Moira enjoyed using a strapon when she Dommed me. I had also been used anally often during scenes when she and I played with others.
The fire began almost immediately as the “lube” did its job. She wiped the excess liniment remaining in her hand off on my scrotum, and soon, it began to burn. The searing pain built continually while she moved her focus to my nipples. First, she pinched and twisted them between her beautifully lacquered nails. The pain momentarily eclipsed the fire in my as and scrotum. When she finally tore a cry of anguish from me, she released my nipples and returned to her bag.
The next toy from her bag of tricks was a pair of clover clamps which she snapped onto my nipples, and I rewarded her with a scream this time. I nearly collapsed as my knees threatened to buckle from the agony she was giving me.
My breath came in shuddering gasps as she stood back, admiring her work with a wicked smile gracing her gorgeous lips.
“You are a beautiful sight, baby.”
“Thank you, Mistress,” I managed to choke out as tears rolled down my cheeks.
“Now for some real fun. Kneel.”
I think I actually gulped as I dropped to my knees. She reached behind her neck to open the fastening of her dress and began to lower it teasingly. The sensual way she slowly revealed her extraordinary breasts made me forget the pain momentarily. They were perfectly shaped, with succulent nipples I immediately yearned to take into my mouth.
She knew what effect they had on me. My throbbing erection amped up her beguiling smile. Then she proceeded to lower her dress to the floor. She was a fantastic sight in her spike-heeled boots and french cut black silk panties. Using just her thumbs, she slid them down over her hips with excruciating slowness. I was panting by the time they dropped to the floor at her feet.
She stepped close to me, reached between her legs, and released her cock from whatever had been securing it. And what a cock it was. I had never seen anything like the massive appendage hanging before my face. Her cock was long and thick and just beginning to grow. The tip of her glans tickled my lips as it erected. I kissed it, and she murmured, “Good boy, now suck it for me.”
Even half-hard, it was difficult for me to open my mouth wide enough to take her in.
I managed and began swirling my tongue around it, teasing her pee hole with the tip of my tongue. Amazingly, she kept growing in my mouth. I struggled to keep my teeth away from her swelling flesh.
“Take as much as you can, slut.”
I forced my mouth down on it until it reached the top of my throat. There was no way I could take any more. It would be like swallowing a baseball bat. I reached up to caress her appropriately sized balls. They were nearly the size of tennis balls.
She stroked the back of my head and pressed me forward so the glans
began to enter my throat, but I gagged and pulled back.
“We’ll need to train you better. Anyway, there are more ways to skin a cat than just one. Stand.”
I struggled to my feet, and she immediately grabbed a handful of my balls. She dragged me to the bed and pushed me down on it face first, using them as a handle. Her alacrity in securing me with the restraints was stunning, and I was quickly at her mercy. I struggled against them, but it was useless.
“Mistress, please, don’t…”
“Ssh, relax, don’t worry, I’ll be gentle.” I continued to struggle, sure of what was coming next and terrified by the size of her giant cock.
She pulled the plug from my ass and whispered in my ear, “Do I need to gag you with this, or will you settle down and enjoy it?” She rubbed the plug against my lips as punctuation.
I took her threat seriously and lay still while she thankfully applied lots of lube to my ass, and it felt as though she coated her cock with it too.
When her glans popped past my sphincter, I cried out. She was good to her word and didn’t slam the entire length of herself into me at once, but by the time she was most of the way in, it felt as though I were being split in two. Surely when she drove it all the way home, it would pop out of my mouth.
She began fucking me then, long, slow strokes at first but then more insistently, pumping that monster into me. At first, it hurt horribly, and I could taste the tears she was wringing from me, but strangely it began to feel wonderful as her cock hit a spot deep inside me that had never been touched before.
I felt her tempo and the force of her thrusts increase along with her breathing. Small grunts accompanied this, obviously signaling her impending orgasm. As she pounded into me harder with each stroke, I began to climax, shooting stream after stream of cum onto the bed, and as I came, I felt her drive deep into me and explode into her orgasm, flooding my ass.
We lay together, spent and still rushing with the ecstasy of our shared passion for several minutes. Her cock gradually deflated, reducing the discomfort until it became a comforting presence filling me. When she eventually pulled out, the void created made me crave that delicious fullness again.
“We are going to have a wonderful weekend together, my little cockslut.” She whispered into my ear before rolling off of me. I wondered how Moira’s adventure was going and if she had found the eager fists she hoped to find. For my part, I thought about Mistress Cassandra’s cock and how close it might be in size to Moira’s fist as I drifted off.