BDSM Again!

Story Info
Crossdresser Maria returns to the BDSM club!
4.7k words
4.52
4.1k
2
Story does not have any tags
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I was sitting at the bar of the hotel chatting with Thomas, the bartender, enjoying my usual brandy. The Dionysus was meeting tonight, and I was going to attend. The Dionysus was a floating BDSM club. I discovered it with a big assist from Thomas. Andrew, the founder, had given me a lifetime membership that I had activated not long ago. I had promised to come back sometime and spend the night with him. I was hoping tonight would be that night.

I had taken quite a bit of time choosing what I hoped would be just the right outfit to entice Andrew. I was wearing a sheer, see-through long sleeved black blouse. Underneath, I was wearing a black leather bra with cut out nipples. My silicone breasts peeked perkily out of the openings in the bra and were easily seen through the sheer blouse.

I wore a black leather pencil skirt, when I sat down it came to mid-thigh. Underneath, I wore an eight strap, black leather waist cincher. I had on a black leather thong; the garter straps were threaded underneath it. They were attached to sheer, jet black stockings. I wore black leather knee-high boots with 5" stiletto heels. On my hands were black leather, fingerless gloves. I wore four deep purple topaz rings, one each on the pinky and index fingers of my left hand and ring and middle fingers of my right hand. I had on dangle earrings, shaped like an Egyptian ankh and also made out of purple topaz. I wore a 3" wide black leather dog collar.

I had chosen a deep purple wig, cut in a bob. I matched my makeup palette to the wig's color, including eyeshadow, rouge, lipstick, and nail polish. I added 2" nail extensions; I never wore my nails that long, but I was going all out tonight.

Every unattached man who came into the bar, took one look at me, came right over and asked if he could buy me a drink. I was like a lone flower in the field that all the bees headed for. I saw one woman walking in front of her husband come into the bar and as soon as she saw me, she turned around, took him by the elbow and led him out. That made me giggle and feel really good about how I looked. When a woman doesn't even want her husband to see you, you know you've got it going on!

I finished my drink and sauntered to the private elevator. As soon as the two security guards saw me approaching, they knew I was headed their way. I fished my lifetime membership ID out of my black leather shoulder bag, they took one look at it, both of them smiled at me and escorted me onto the elevator. I pushed the lone button, and it took me to the ballroom where The Dionysus was being held that evening.

I walked to the nearest bar to get a brandy and unlike the last time, walked around mingling and people watching. Truthfully, my outfit was pretty tame compared to the rest of the crowd. Most people seemed to have their own clique but were friendly enough to smile or nod. A hand squeezed my elbow and I turned to look into Andrew's eyes. He was the only man in the place wearing a tuxedo. He said it was a nod to his age, but he made that tuxedo look damn good!

Andrew was almost twice as old as me but was extremely handsome. He had silver hair, hazel eyes, was a little over 6' tall and weighed probably 190 lbs. He was in great shape; he had told me last time that he was into yoga and tai chi which accounted for his fabulous body and unbelievable cardiovascular conditioning for a man his age. "My, that's a much different look for you. Is this your way of letting me know you're looking for something a little more daring tonight?"

I put my arms around him, brushed my lips against his, and said, "No. Actually, just the opposite. When was the last time you engaged in just straight sex? No restraints, no toys, no paddles, no groups? Can you even remember the last time like that?"

He thought a few moments and said, "Honestly, no, I can't remember. I could try and guess but that's all it would be, a guess. Why do you ask?"

"Because that's what I want tonight to be if I spend it with you. Just you and me, two people who want to pleasure one another and use only their own minds and bodies to do that." I pressed myself against him and kissed him passionately. "This is just a promise of things to come."

He kissed me back and said, "We shall see. In the meantime, I would love for you to be my arm candy as I make my rounds greeting the members." He held out his arm to me and I slipped my hand through his extended elbow. He took me all over the ballroom, saying hello to everyone by name. There were some people who were covered head-to-toe in their leather outfits; I had no idea how he knew who it was, but he did!

Almost as soon as I finished my drink, a waiter, naked except for leather chaps, magically appeared to take my empty glass and give me a full one; I hadn't even had to order. I smiled and nodded my appreciation. I looked at Andrew and said, "There are benefits to being with the founder of The Dionysus I see, benefits I hadn't even considered."

He smiled at me, gave me a kiss on the cheek, and continued his conversation with a group of leather clad people who seemed so intertwined, it was difficult to tell where some of them started and some of them left off.

We continued walking and a woman wearing only a leather thong, pasties, and platform heels came up to us. Andrew greeted her and she returned his greeting. But she turned to me and said, "I'm Candy, I'm guessing you must be Maria. Ingrid told me all about you from your last visit here."

"Yes, I'm Maria. Ingrid told you about me? I hope she had good things to say."

"Oh girlfriend, you have no idea! I've never, ever heard her mention the idea of hooking up with someone a second time, but she definitely wants to get together with you again. And she's hoping she can have you all to herself and not have to share you with Andrew!"

I blushed deeply but thanked Candy. I looked at Andrew, but he just smiled. "I think you underestimate yourself darling. I'm not sure you realize just how hot, how sexy you are."

"Andrew, I just enjoy what I enjoy. And I want the people I'm with to enjoy it too!"

"It is exactly that carefree attitude and wanting others to have as much pleasure as you that makes you so desirable."

We mingled for another hour or so, everyone knew Andrew, everyone wanted to at least say hello to Andrew, even if they didn't stop to talk. Andrew had been carefully leading us to the back of the ballroom, where an express elevator to the penthouse floor was. He had casually called the elevator; I didn't even realize it was there until he guided me onto it. He pressed the button to take us to the penthouse suites.

"I'm assuming if you're taking me upstairs that you intend to honor my request. Just you and me, just our bodies and our imaginations."

Andrew smiled at me and said, "I have to admit the idea of 'straight' sex is fairly erotic in its own right given my sexual preferences. Yes, darling Maria, we're going to do things your way tonight."

I pressed myself against him, kissed him hungrily, and pulled him by the ass cheeks to me. He returned my kiss and pulled me to him just as needily. The elevator arrived at the penthouse floor, Andrew and I walked hand-in-hand to his suite. He unlocked the door, and we walked inside.

He took me straight to the master bedroom, past the room with mirrors for walls and restraints hanging from the middle of the ceiling and attached to the floor directly underneath. We walked inside, he stopped, looked at me and said, "Well?"

There was a wide hallway just inside the doorway to the bedroom. It was lined with closets on one side. Those closet doors all had full-length mirrors on them. I stopped us there. I started to undress Andrew, helping him out of his bowtie and tuxedo jacket. I removed his cummerbund and tuxedo shirt; he was naked from the waist up. I leaned in and began to kiss, lick, and suck his nipples. They became hard almost instantly and he put his arms around me, pulling my face to his chest.

I pushed away from him. "No, no, no." I said playfully. "Right now, I want you to keep your hands to yourself. Just concentrate on the feeling of me pleasuring you. And watch me, watch us in the mirrors."

He smiled at me and nodded. I knelt in front of him and helped him out of his shoes and socks. My hands went up his pants legs and I was massaging his calves. I knelt down even further and began to lick the tops of his feet. I was licking in between his toes. When I glanced in the mirror, I saw that my skirt had ridden up and the tops of my stockings attached to the garters were showing in the back. I could see Andrew had noticed as well and I smiled at him in the mirror.

I lifted up one foot, he placed his hands on my shoulders for support. I started sucking his toes, one at a time. It was like I was giving a blow job to each of his toes! I did the same thing to the other foot and Andrew was moaning appreciatively. I set his foot back on the ground and reached up to unbuckle his belt, unzip his pants and slide them off him. He was standing in front of me wearing only a leather thong. I giggled and said, "I see you have to give at least a nod to your history as the founder of The Dionysus."

He just smiled at me. I stood up and began to unbutton my blouse, slowly because I was not used to the 2" extensions on my fingernails! I let it slide to the floor. I reached behind me and unfastened and unzipped my skirt. I slid that down my stocking covered legs, past my boots, and stepped out of it. I bent over, deliberately facing Andrew, to pick up my skirt and blouse. I strolled over to his pile of clothes and dropped mine on top of his. I walked back over and stood in front of him, just out of arms reach.

I blew him a kiss, licked my lips and began to pull my leather thong past my hips, down my thighs, past my knees, calves and ankles until it was on the floor. I was staring into his eyes the entire time I did. I stepped out of it and kicked it over to the pile of clothes. Still staring into his eyes, I began to play with my silicone nipples and vagina, fingering myself while rolling my nipple between my painted fingernails.

We both knew I couldn't feel anything, but it was about the visual, the aural. I was moaning and shivering as I 'played' with myself in front of Andrew. "Oh yes, Andrew, yes baby. I love masturbating while you watch, I'm getting so hot watching you look at me while I play with myself." I pulled the nipple I was playing with up to my mouth and began to tongue it and suck on it. Andrew was rubbing himself through his leather thong.

I stopped what I was doing and walked over to kneel in front of Andrew. Gently, I pulled his hands away from his crotch. I reached up and began to pull his leather thong down in exactly the same way at exactly the same speed I had pulled mine down. His 7" cock was at full attention when I got his thong past his hips. I ignored it and continued to pull his underwear down and off his body.

I began to lick his ankles, moving my way up his legs, first one leg, then the other. My 2" fingernails were faintly scratching the backs of his legs at the same time. When I was kneeling upright, I was staring directly into his throbbing erection. I looked up at him and just smiled. I licked his scrotum and the underside of his penis slowly as I continued to stand up. My nails were rubbing his ass cheeks. I continued to kiss the front of his body, caressing his back with my fingernails but now I was starting to press my breasts up against the front of him, rubbing his body with them as I stood up.

Finally, I stood up, pressed against him. His cock was throbbing; I reached down to wrap one hand around it. I leaned in to kiss him hard and thrust my tongue into his mouth. He accepted me hungrily and pulled me into him, his hands cupping my ass cheeks. I was stroking him until he finally pushed me away. "No, baby, no. I feel like I'm going to cum and I don't want to do that like a teenager getting his first hand job. Take me to bed, please!"

I put my hand in his and walked ahead of him so he could continue to get a good look at me in my leather lingerie, nylons and boots. I laid him down on the bed and knelt between his legs. I wrapped my purple lips around his prick and didn't go any lower. I swirled my tongue underneath the rim while my painted fingernails explored his body. He put his hands behind my head and tried to pull my mouth down his shaft, but I reached up and gently pushed them to his side. "Andrew now is the time to just lay back and drink in the sensations. Don't try to force anything, baby, relax and enjoy!"

I resumed just sucking and rimming his prick. With one hand I began to gently run a fingernail from his asshole to his scrotum along the perineum. With the other hand, I began to jerk him off into my mouth while my lips were wrapped around his head, licking and sucking just the tip of him. Andrew came, suddenly and violently. His body spasmed as if he was being electrocuted. A torrent of his hot love juice spewed down my throat. I swallowed it all eagerly and continued to suck his prick, licking the slit through his orgasm until it subsided. He collapsed on the bed.

I crawled up to be in his arms and cuddled with him. I was kissing his face and neck gently. "Mmmmmm, baby, you taste so good. Maria loves to swallow every drop her man gives her."

Andrew was holding me to him, one hand running through my hair, the other cupping one of my ass cheeks. "I do believe this was a good decision on my part. Your foreplay and technique are unparalleled!"

I slapped his chest lightly with one hand. "Do you have to be so damn clinical? Can't you just enjoy the moment?" I asked.

"Don't forget who you're with, my dear. I'm a businessman and my business is sex; I can't turn that part of my brain off. Remember what Candy told you about Ingrid. You have NO idea how incredible it is that Ingrid wants to be with you a second time!"

"Well, put that part of your brain on hold. I want your mind here with me, all of it, 100%. You can dissect tonight later but I want your attention, all of it! And BTW. You have a hallway lined with mirrors. You have a room full of mirrors. But there aren't any mirrors in the damn bedroom itself! WTF is up with that?"

"I don't spend much time making love in the bedroom, that's just much too pedestrian." Andrew smiled wryly.

"Get the hotel to add a wall of mirrors next to the bed, you might be surprised how much it spices the bedroom up!" I said.

I yanked the thick comforter off the bed along with a pillow and started dragging them out of the room and down the hall. "Where are you going with that?" Andrew asked.

"I'm going to lay the comforter down in the hallway with the mirrors." I replied. "I'm not going to get rug burn if I can help it!"

Andrew followed and helped me put the comforter down. "I'm also going to guess you probably can't remember the last time you fucked in the missionary position." He smiled and nodded. "That's what we're going to do. Let's lube each other up in the sixty-nine position. Top or bottom?" I asked.

Andrew lay down on his back. I climbed on top of him with my ass in his face. I grabbed his cock and started licking and sucking him, letting my saliva drool up and down his shaft. Andrew pulled my ass to his face. His lips rimmed my rosebud and then something crazy happened. Andrew was one of those people who could roll his tongue. He started tonguing inside me with his tongue rolled. The sensations were electric.

"OH Andrew! Eat my pussy, baby, mmmmmmmmm, yes, yes, yes, yesssss! Oh shit, oh fuck, baby you're going to do more than lubricate me, I'm going to cum for you!"

Andrew wrapped his hands around my nylon-covered thighs and began to massage them and pull my ass even closer to his face. I love when a man is stroking my stocking-clad legs. Andrew knew this and continued to do so while he was tongue fucking me. I lost complete control and had a mind-numbing orgasm.

"Nnnnngggggghhhh, shit, fuck, oh, oh, ohhhhhhhh. Eat me, eat my pussy, eat me, eat me, eat meeeeeeeeeeeeeeeeeee!"

Andrew continued to eat my ass and rub my legs through my orgasm. I collapsed on top of him. "Damn, baby. We were just supposed to lube one another, and you make me cum, hard!"

"Would you like me to take it back?" Andrew asked.

"Oh baby, no! I want to keep that orgasm. I also want you to fuck me now, fuck me hard. Make me cum again for you, baby!"

I laid down on my back with my head facing the mirrors. I put the pillow under my ass propping it up for Andrew. Andrew knelt in between my legs; he would be watching us in the mirror. He put his hands on the ground. He had my legs pinned by his elbows, pushing my ass even higher in the air. He gently slid his prick inside me and then.... just stopped. I waited for a few seconds and said, "Andrew? Are you going to fuck me or not?"

He just smiled at me and didn't say a word. Just his prick was in my asshole, he had me in a position where I really couldn't move. I tried to slide my hips up the length of his shaft, but he wouldn't let me. "Andrew? Baby? I really want your cock, please give it to me baby, I need you to fuck me!"

Andrew continued smiling and not talking. I became acutely aware of the feeling of his mushroom just inside the entrance to my love hole. I became acutely aware of his elbows pinning my legs so they couldn't move. I desperately wanted Andrew to fuck me, I was aching for Andrew to fuck me, but he just held me like that and didn't move.

I arched my back and looked at us upside down in the mirror. I was Andrew's fuck toy, and he was completely in charge. Looking at us, feeling him inside me like that, feeling him in complete control of my pussy pushed me over the edge and I began to cum again, even more explosively than when he ate my ass.

"A-An-And-Andrewwwwwwwwwww! Shit, baby, shit, baby, fuck, fuck, fuck, FUCCCKKKK! Cum-cum-cum-c-c-c-cummmminnnnngggggggg!"

When Andrew heard my orgasm begin, he began to fuck me hard, really hard. He was ramming my pussy, sliding into me until he bottomed out and his balls were slapping off the cheeks of my ass. I was still unable to move, he held me in place and continued to pound my ass. I reached around and grabbed his ass cheeks, pulling him into me as deep as he could go. I was begging him, "Fuck me with this hard cock, pound this pussy. Fuck this pussy, take me, take all of it! Fuck Andrew, fuck Andrew, fuck, fuck, fuck, fu-fu-fu-fuck mmmmmmeeeeeeeeeeeeeeeee!!!! Please Andrew, please, please, please, PLEASE!!!! Aaaaaahhhhhhhhhhhh!!!!"

Andrew just continued to piston in and out of me; I was in an orgasmic fog for a few moments. When I finally stopped cumming, I began to fuck Andrew back, just as hard. I wrapped my legs around his waist and continued to pull him into me as deeply as he could go. I started rotating my hips around his shaft as he continued to drive in and out of me. Now I could tell Andrew was starting to lose control; his cock began to tremble and throb inside me.

"Look at us fucking, Andrew. Look at you fucking me hard. Look at the way I'm dressed just for you! I want all of your cum Andrew, I want you to fill me up. I want so much of your cum inside me it starts overflowing and running down my thighs. Fuck me, Andrew. Fuck your hot slut bitch. Fuck hot slut bitch Maria. Fuck her, fuck her, fuck her!"

Between my ass squeezing / riding his shaft and my dirty talk, Andrew began to cum.... in buckets!

"M-Ma-Mar-Mariaaaaaaaa!!!! Fuck, fuck, fuck this pussy, fuck this pussy, love this pussy, want this pussy, this pussy is so fucking HOTTTTTTTTTTTTT!!!!!!!!!!!!!!!! Cum, cum, cum, cum, make me cum, Maria, make me cummmmmmm!!!!!!!"

Andrew unloaded inside me. He filled me up and continued to cum, his hot sperm was dripping down the crack of my ass onto the comforter beneath me. Andrew collapsed on top of me, he was spent. I held him in my arms and kissed his face, neck, and ears until his orgasm subsided.

12