Hi, I'm Marie, a 50 year old woman at the dawn of her sexual RE-awakening. This story is a continuation of Maestro Dominates Marie's Ass. I thought I'd experienced the best anal ever that afternoon. Little did I know what Maestro had in mind for my ass that night...
As I laid by the pool, feeling the prickly hot Mexican sun on my back, my thoughts wandered back to how I had arrived at this moment with Maestro.
Less than six months ago, I thought I was done with sex. I was stagnant, unsexy, and I didn't even want to masturbate anymore. Then one day everything changed when Maestro, the man who for years had sat innocently across the desk from me at work, shook me to my core and turned my whole world upside-down. He taught me about all of the fantastic, kinky sexual pleasures that I have been missing out on and had only existed in my fantasies. I learned the joy of sexual freedom, and defying taboo and my own insecurities. With Maestro as my teacher, guide, and TERRIBLY naughty influence I decided to experience it all and share the TRUE stories of my dirtiest confessions.
And some of my dirtiest fantasies involve my ass.
Maestro and I had reached the middle of our 10-day holiday at a fabulous resort on the Riviera Maya in Mexico. We had spent previous days drinking, flirting with women, getting horny from flirting and going somewhere to fuck or finger or play, and repeat. My asshole was still tender from Maestro's insane pounding only a few hours earlier, and now he was laying next to me on a sun lounger on the 3rd floor lounge having a chat with Skrillex (I'm calling him Skrillex because that's his favorite DJ), our favourite pool boy, about hip hop music. I decided to lay on my stomach, worried that his cum might leak out of my ass all over the towels and lounger. It felt a bit uncomfortable, like I was struggling to regain control of my anus. Maestro glanced over occasionally with his wicked grin, watching me wriggling around, trying to find a comfortable position. His cock bulged slightly under his tight swim shorts. He was, I'm sure, like me - replaying scenes in his head from the best anal sex we'd ever experienced.
Maestro, as you may already know, is a wild one. He does not bow to convention; convention bows to him. He always dresses impeccably, with some accent. Today it was a pair of wooden sunglasses matched with a wooden watch. As Skrillex left to greet another client, Maestro rolled on to his side.
"It is called zebra wood, Marie, not that it matters but doesn't it look nice in the sun?"
"Mmm, yes, Maestro. You can pull off almost any look!"
I swear it's his attitude. He always swaggered around the hotel, using kindness and listening with genuine interest to guests and staff as they shared their stories, throwing in a few of his own - sauced liberally with humour.
"I've been on a bit of a roll today, haven't I? Did you hear Skrillex laughing? I'm feeling pretty good from all of the attention, and I always love showing you off to everyone, my sexy little fucktoy... especially after the treatment I gave your ass this afternoon. Seriously Marie, it's still hard to believe that only a year ago we were just professional colleagues at work, platonic friends with no thoughts about that boy/girl sitting across the desk! I thought about your pussy occasionally, but nothing as perverted and twisted as what I'm thinking right now. And reading your stories always make me so horny. And you know what happens to you when I get horny, darling..."
"Oh Maestro," I laughed. "You have incredible stamina! My body still needs to recover a bit."
"Recover? Do you think you deserve recovery time, Marie? Really?" Maestro's devilish grin told me I wouldn't be resting. "Come over here onto my lounger. There's room for both of us, and look - there's no one else around except Skrillex. I'm going to play with your asshole while you write the rest of your story; to get you warmed up for the pounding I have in mind for tonight..."
"Oh god...MAESTRO! Here?" I looked at him with an incredulous smile. I barely had enough strength to lift my head off my lounger before he sat up and moved over.
"Now, Marie. I want you next to me NOW. You're not going to disobey me here are you?" A hot breeze blew across my back and settled, like a light blanket being thrown over me. Every inch of my body wanted to continue snoozing on my lounger, but Maestro's cock was more visible behind his swim shorts, stirring as he gazed down the length of my bronzed body. And I know this tone of voice. He wouldn't hesitate to punish my ass further despite our intense anal session only hours ago. I scrambled up onto my knees, adjusted my sunglasses, and reached behind me to finger my ass gently. Just to make sure I wasn't still leaking cum. I was closing up a bit, but still far more distended than ever before.
"OK, let me just grab my towel. Are you sure..." Maestro's kiss stopped my question from escaping. As soon as I shuffled over to his lounger, his hands reached out to caress my windswept hair, before kissing me passionately, deeply. He caught me as I lurched awkwardly down on his lounger and enveloped me in kisses beside him. Maestro's way of alternating between dominance and control and romantic tenderness leaves me feeling like a heroine of a bodice-ripping romantic novel. His libido overwhelms me, making me submit to his erotic imagination. Quite frankly, I turn to mush.
"How is your asshole now, Marie? I bet it's not the same tight little hole as yesterday. Mmmm, no... no, baby, you don't have a tight virgin ass anymore." His long fingers slipped under my bathing suit bottom as I lay on my side, resting my head against his shoulder. He probed my asshole with his index finger, around and around, but careful not to push inside. Beads of sweat dripped down my back, moistening his finger. Or was it my pussy juice? His exquisite foreplay made me horny, despite my body's yearning for a rest. "Oh that's a good girl, Marie. My good little sextoy. You just can't resist a little anal tease, can you?" Two other fingers joined the party as now three of them now rimmed my asshole, pressing hard enough to make me moan but never inserting them fully.
"Maestro, oh fuck. Mmm, my asshole won't close up. I don't know if it will ever be the same, I feel sooooo stretched out." Our eyes locked together, oblivious to anything else but our bodies moving in unison. "Oh dear god, I can't believe I'm so horny again! All I want is your cock, darling, just to feel your cock fill me up. My pussy, my ass, my mouth - I don't care, Maestro!"
"Oh I know, Marie. I know how horny you get. I know how to tease you, how to make you cum. Don't I?" He pushed his middle finger in my ass, as if to punctuate his last question. At the same time he pushed me on my back slightly, hiding his hand now visibly playing beneath my swimsuit. Skrillex's voice rose above the din of the reggaeton hits blaring from the speakers below, practicing his English on another couple settling in to sun loungers just behind Maestro. They were focussed on sunscreen and water bottles, not noticing the fact that I was getting anal fingered just in front of them.
"Like this? And this? Oh, there you go... oh yes... yes, Marie!" Maestro's cock, now fully erect, pressed against my clit on top of my bathing suit as his middle and index fingers stabbed my wrecked and loosened asshole. He rotated his fingers inside of me, pressing against the thin wall separating my ass from my pussy. I rubbed my clit against his cock harder, our swimsuit bottoms barely concealing our lust.
Maestro usually fucks for hours and hours, but the thrill of being outside and perhaps getting caught stimulated our libidos beyond any sense of propriety. I grabbed a towel, tossing it over our hips just as I started to cum. My pussy juice smeared over Maestro's swimsuit as I loosened it and released his massive cock. He withdrew his fingers from my ass and pushed my bikini bottoms down to reveal my freshly waxed pussy, nicely hidden beneath the towel. "Oh fuck, Marie, I'm going to make you cum again!" Maestro whispered in my ear, gripping my clit with one hand and his cock in the other. Creamy cum dripped between his fingers as I buried my face against his shoulder, at the same time I felt his hot cum spray onto my belly.
The couple behind us chatted on about their flight from London, how the hotel messed up their room booking, and the lack of decent rum in any of the hotel bars. We adjusted our swimsuits and tossed the cum soaked towel aside, confident that they hadn't noticed us at all. "Maestro that was insane! They could've seen us... Skrillex could've seen us... that was such a fucking turn on!" I whispered back to Maestro, running my fingers up and down his chiseled abdomen.
"You doubt me, Marie?" Maestro laughed. "I know you're an exhibitionist, almost more than I am. I can make you cum in an instant if there's people around."
"I don't doubt you at all, darling, I know better than that! But I'm exhausted now, and I want to see that band later tonight."
"Well, let's have dinner and a dance, then, at least to start the night..." Maestro grinned, "And then we'll see how your ass is doing."
The band started the first set with Hotel California. Not exactly a song to get people up and out of their chairs, but Maestro grabbed my hand and we danced and sang along. We knew the lyrics better than the singer, who was flipping pages furiously to keep up. By the time we got to "... you can check out any time you like, but you can never leave..." we were joined on the dance floor by two beautiful women. Both were dark-haired and voluptuous, and one woman wore only a tiny thong bikini with her perfect round ass on display. She smiled at me, and we danced as women often do at clubs together. Our flirtatious dirty dancing - my hands on her hips as I pressed my nipples against her back, her hands on my thighs - provided a show for onlookers, including the band. Not long after that, a crowd of single men flooded the dance floor. Their awkward and uncoordinated but enthusiastic moves contrasted with the women's rhythmic, mesmerizing, undulating hips. They laughed as the men tried to look sexy, but the woman in the bikini only had eyes for Maestro.
Aware that Maestro and I occasionally kissed and danced together, she approached me to try to communicate. I couldn't understand her at all, and being a bit tipsy from double vodka and cranberry juice highballs, was totally oblivious to the fact that she was asking if we all wanted to go and fuck. I was still so innocent with women. SO innocent! I've danced sexy with women before at clubs, but not because I wanted to have sex. It's just a fun, flirty thing to do - mostly to tease all the men. So by the time the band ended their set with a rousing version of Don't Stop Believin', the women were gone.
"Everyone's clearing out now, and dancing with those women made me horny, Marie," Maestro purred, "Did you think they were hot? You didn't want to play with them? They totally wanted to play with us! They didn't speak English, but the woman in the dress made it clear what they wanted."
"Seriously? No way! Oh fuck... I completely missed that. I had no idea what she was trying to say, and I just blew her off. I didn't know what she was trying to say! Fuck, Maestro, I messed that one up. They were hot too..." I sighed, realizing we could've been playing with her fantastic ass had I been more aware of non-verbal pick-up cues.
"Well you know what that means, Marie. You've got to take it all yourself. All my energy, which would've been spread out among two or three women is all yours now." Maestro gripped my waist and pulled me closer to him as we took the elevator up to the 8th floor. "I'm just deciding now whether to destroy your pussy or your ass," he growled into my ear.
I knew whatever I said wouldn't matter to Maestro. I knew that tone of voice. He was going to dominate me that night. He was going to use my body - OWN my body for his crazed sexual pleasure. And I was his willing fuck toy. Still, I pleaded with him to be easy on me, even though begging Maestro at this point would be futile. "Maestro, you fucked my ass so hard this afternoon, I don't know..." As the elevator opened to the 8th floor lobby, Maestro slipped his hand inside my dress, squeezing and twisting my left nipple hard. "Oooohhhh... owwww... oh motherfucker fuck fuck fuck that hurt!" He released my nipple, stroking it softly now.