Halloween Gone Wrong!

"Oliver, I'm guessing that's something else Ken told you about me!"

Oliver smiled as he took my hand and led me to the dance floor. I'm sure we looked unusual. The 'woman' who looked like a $1,000 dollar-a-night hooker and the obviously very rich man who was clearly more than twenty years her elder. I did not care. I loved to dance. Oliver was very accomplished. Not the best partner I ever had but he was smooth and polished. When we finished our Salsa dance, we got a very polite round of applause from all the other patrons in the bar.

We continued our conversation. Oliver was a very nice guy when he wasn't being such an asshole. "Oliver, why the charade? Why play-act at being so tough and so mean? You're a good person. You're actually very nice."

He wouldn't look at me directly. Oliver was staring into his drink on the bar when he spoke. "At the end of the day, I have to take responsibility for my own actions. I could blame them on a loveless wife who I adored when we first got married but turned out to be a gold digger. She used me. The moment I said, 'I do' she said, 'I don't anymore!'

My parents got divorced when I was a toddler, I don't even know my father. My mother had to work two jobs just to keep a roof over our heads and food on the table, so I didn't see much of her either. I pretty much raised myself.

I learned how to turn off my feelings early on to protect myself from emotional pain. And now you're sitting next to the cold bastard who tried to use you and Ken last night for his own personal pleasure."

I put my hand on Oliver's thigh, leaned in, and kissed him on the cheek. "I'm truly sorry, Oliver. But Ken was right, and you know it. The guy who built his business is still inside you. You can still be a successful businessman without being a flaming asshole!"

I handed him the envelope back. He looked confused. "Maria, what is this? I gave that to you to prove I wasn't going to blackmail you into having sex with me."

"And I believe you, Oliver. I'm not going to hold this letter over your head with you wondering if I was ever going to use it against you. Sometimes, you just have to trust people."

Oliver took the envelope, licked it, sealed it, and signaled the waitress. "Young lady, could you please take this envelope to the office, and have it shredded? There's a $50 tip waiting for you when you come back to tell me it's been done."

"Easiest $50 I'll make tonight." she replied. She walked away and came back just a few minutes later empty-handed. Oliver tipped her $100. She beamed at him and returned to her job.

"That was nice of you, Oliver. You made her very happy. How did that feel?"

"I'm not sure. I'm still new at this but I think I feel pretty good about treating the waitress even better than she expected."

I laughed and said, "You'll learn, Oliver, you'll learn."

We continued to chat and dance, while Harold kept our drinks fresh. It was getting late. Oliver and I were dancing to a slow song, he had both of his hands on my hips, and I had both of my hands on his shoulders. One of his hands wandered down and cupped the cheek of my ass. He began to massage it absent-mindedly. I raised an eyebrow but looked at him and smiled. He realized what he was doing and immediately put his hand back on my hip. "I'm so sorry, Maria, I'm so sorry."

"Oliver, I'm not offended. It's nice to know you're attracted to Maria." I looked into his eyes and kissed him gently on the lips, allowing my tongue to play over his lips while I kissed him.

He looked back at me, more than a little surprised. "Maria, does this mean what I think it means?"

"Oliver, these are brand new boots. It's the first time I've ever worn them. I feel so damn sexy in them. I've seen the men in this lounge drooling over me and that fucking turns me on. My pussy is wet. I want them wrapped around some man's back while I'm screaming in orgasmic ecstasy."

Oliver's eyes lit up and he had a huge smile on his face as we walked back to the bar. Oliver paid our tab and left Harold a very generous tip. I led him to the elevators, and we went inside to go up to my room. As soon as the elevator doors opened, I molded my body to Oliver's and kissed him hungrily. This time I pulled his hands to the cheeks of my ass. He pressed me against him and returned my kiss with a fire that surprised me.

"My, my, my! How long has it been since you've been with a woman, Oliver?"

"One I haven't paid to be with? Longer than I care to admit."

The elevator stopped and an elderly couple got on. The woman stared at me icily, I was still molded to Oliver's body with my arms wrapped around him. They got off on the next floor and we could hear her say to her husband, "Well, I never, Bob. And this used to be such a nice hotel."

As soon as the doors closed, I started giggling. "What's so funny, Maria?"

"Well, I never, Bob!" I said mimicking her. "I wonder what she would have said if I would have reached over and rubbed my hand all over Bob's crotch." I continued to giggle. "There you go, honey. Bob's ready for you now but he's going to close his eyes and pretend it's me!"

"You can be a naughty girl but it's also very obvious you're comfortable with your own sexuality and you enjoy it."

"Sex should be enjoyable, Oliver! And fun! How can something so enjoyable not be fun?"

The elevator doors opened, and I led Oliver to my room. "Would you like something to drink, Oliver? From the look on Harold's face, I'm sure I don't have what you ordered downstairs, but I do have a small wet bar."

"A gin and tonic, Maria. Any gin will do, I promise not to be picky."

"Please, have a seat on the couch." I said as I poured us drinks. I took my time. I wanted to let Oliver get a good look at me in the full light of the room. I sauntered over to him slowly as he stared at me and licked his lips. I gave him his drink and snuggled in next to him. We began to share more of our life stories with each other. Oliver's was way more interesting, and way more painful. I could understand more of why he had done what he did last night. That still didn't excuse his actions, but I could understand them better.

I got up to pour us another drink. I could hear a sharp intake of breath behind me. I stopped and looked over my shoulder at Oliver. He was pursing his lips and just staring at me, drinking the sight of me in. I posed with one hand on my hip; and winked at him licking my lips seductively with a promise of what the immediate future might hold. When I returned to the couch, I sat even closer to him, molding my body to his.

I leaned over and took his earlobe between my lips. I nibbled and tongued it. Oliver was definitely getting turned on, I could tell by his shallow breathing. I allowed my fingertips to trace the outline of his hardening cock. Oliver hugged me to him and put his hand on my leg, running his fingertips just under the top of my boot and caressing the nylon leg underneath.

"Oliver, oh Oliver. I love that, move your hand higher, baby!"

Oliver obliged and found the top of my stocking where it was attached to the corset's garter straps. He turned his face to mine, and I kissed him full-on. He kissed me back with no hesitation. Oliver put his hands under me and lifted me up, so I was sitting in his lap facing him. His hands were all over me as we made out like two wanton teenagers. Both hands began to caress my thighs and I was sucking on his tongue furiously. My fingers were rubbing his now throbbing erection underneath me.

My breathing was starting to get shallow; I was getting really turned on. I stood up and Oliver looked at me puzzled. "Maria, did I do something wrong? I'm sorry!"

"Oliver, you haven't done anything wrong. To use your words from last night, 'I'm just not going to cum like some lovestruck teenager.' You're fucking hot, Oliver. I want to make love to you. Like I told you downstairs, I want these boots wrapped around some man's back while I'm screaming in orgasmic ecstasy. Tonight, that man is you."

"Strip for me Oliver, slowly. I always enjoy watching my man get naked for me."

Oliver began to undress, a little clumsily, a little unsure of himself. I don't think he was used to being with a woman who wanted him the way I did. Finally, he was standing naked in front of me. Oliver was in pretty good shape for a man his age. He was tanned and had only the slightest paunch around his waist.

I leaned over, fondled his balls, and slowly licked his hard shaft from the base to the tip. Oliver was shivering with delight. I stood up and backed away so he could get a really good look at me. I reached down and began to unzip my dress upwards slowly, slowly. When I was completely unzipped, I let the dress fall to the floor behind me and posed for him again.

Oliver was absent-mindedly stroking himself. "Oliver! Don't you do that, that's my job." I said laughing. Oliver realized what he had been doing and let go of his cock, blushing. He seemed more than a little embarrassed. I strode over to him; pressed my body against his and wrapped one of my legs around him. I kissed him passionately as my hands roamed his back and ass cheeks.

Oliver hugged me to him just as passionately. His hands were everywhere. We made out with complete abandon. Oliver was getting really turned on; I could tell he was getting close. I knelt in front of him. Gripping his shaft, I looked into his eyes and said, "I'm not going to let you get into this 'pussy' right away and cum too fast. I want you to be able to enjoy this pussy and I know I want to enjoy this cock. I'm going to suck this cock dry before I let you inside me."

Oliver was moaning and swaying as I wrapped my lips around his cock. I ran my tongue around the underside of his prick knowing how sensitive the rim is. One hand fondled his balls while the other ran the length of his perineum from scrotum to anus and back again, over and over. Oliver began to tremble, and I could tell he was close to cumming. I began to bob up and down, licking his shaft as I did so. Oliver's hands were on the back of my head, pulling my face towards his shaft.

"OOOOOOHHHHH!" Oliver exploded into the back of my throat. I drank his cum happily and continued to suck and lick him while my fingers continued to massage him. "Maria, Maria, oh shit Maria. Fuck, fuck, fuck. Maria, Maria, Maria!" I drank him dry as I promised. When he was spent, I stood up, walked him to the bed and laid him down. I laid down beside him and we cuddled.

"Maria, that was fantastic. I couldn't believe it. You drove me to explode so quickly. And what you were doing while I was cumming was unbelievable. I couldn't think of anything but the feeling of your lips, tongue and fingers. Holy shit that was so fucking hot."

"Mmmmmm, I'm glad you liked it, Oliver. I always enjoy knowing I've pleased my man."

We just snuggled together, kissing, cuddling, and fondling in the afterglow. I wanted Oliver to know I appreciated just being with him. I could feel him starting to get an erection again, my thigh was pressed against his crotch. "Oliver, I'm going to help you get hard again and lubricate you at the same time, to help you get ready to take this pussy!"

He was lying on his back, and I was kneeling between his legs. I wrapped my lips around his cock and began to lick and suck him back to hardness. I was trying to generate as much saliva as possible so he would be well-lubricated and ready to fuck my ass. Oliver was stroking my hair and groaning; "Maria, this is so hot. I can feel myself growing hard inside your mouth. Mmmm, baby, I can't wait until I'm between your legs. I want that as much as you do!"

In less than a minute, he was rock-hard again, saliva coating his cock. I sat up and asked, "Do you have a position preference, Oliver?"

"I want you on your back. I want to be on top of you. I want you to see my face when I cum so you can see just how much pleasure you're bringing me."

I rolled over. Oliver grabbed a pillow and put it under my hips, elevating my asshole to make it easier for him to penetrate me. I rested my ankles on the cheeks of his ass, opening myself to him. He grabbed his cock and guided it into me, the saliva acting as a lubricant. He entered me slowly, steadily until his belly was against my thighs. We just stayed like that for a little while, enjoying the moment. "Maria! This pussy is so hot, so tight, so inviting."

With that, Oliver began to fuck me. As he fucked me, his hands traveled up and down as he caressed my stockings and my boot-covered legs. When he plunged deep inside me, his hands would slide up until he was holding my thighs. The pinky and ring finger of both hands would slide underneath the welts of my stockings as he massaged me. As he began to withdraw, his hands would run down my stockinged legs until he was holding me just behind my knees. The feeling of his hands squeezing the soft buttery leather of my boots against my nylons was unlike anything I had felt before, I was in sensory overload.

"Shit, Oliver, oh shit. Oh baby, oh baby, oh baby! Oliver, Oliver, Oliver! This is fucking incredible, your cock is incredible, YOU are incredible! Fuck me, baby, fuck me. Oh Oliver, please fuck me!"

Oliver fucked me at that steady pace; his hands roaming my legs with every stroke. I was never more ready to cum. "Fuck, fuck, fuck. Oliver, I'm going to cum, I'm going to cum, I'm cummmmiiiiiinnnngggggg! Shit, shit, shit, oooooooohhhhh Oliver. Mmmmmmm, nnnnnnn, uuuuuhhhhhh. Babyyyyyyyyyyy!!!!" I could do nothing but rock underneath Oliver as he continued to fuck me. My orgasm seemed to last forever as I collapsed, breathing shallowly.

Oliver began to pick up pace; I could tell he was getting ready to cum again. I wrapped my arms around his neck and my booted legs around the small of his back, my stiletto heels digging into the cheeks of his ass. I was suckling his ear as I whispered to him, "Ooooohhhh, Oliver. Mmmm baby, you're so hot, so good. Maria loves the way you make her cum. Maria loves the way you make her feel when your hot cock is inside her. Fuck me, Oliver. Pound this pussy with that hard cock of yours."

Oliver didn't need any encouragement; he began to fuck me at a furious pace. I matched him, thrusting my hips against his as he plunged downwards. His cock began to vibrate inside me and he came furiously. "OOOOOOOOOOHHHHHHHHH, Maria, Maria, MARIAAAAA!!!! Cu-cu-cummmmmiiiiiiinnnnngggggg! Shit, fuck, shit, fuck, shit, fuck. Cum, cum, cum, cum!"

I continued to ride Oliver's cock while he came, pulling him into me with my hands cupped around his ass cheeks. He shot his load, filling my ass up with his warm jizz. He collapsed against my neck, kissing me, tonguing me, nuzzling me. "Maria, oh Maria. That was amazing. Sex with you is mind-blowing. You fuck with abandon. I can tell you really enjoy having sex; I could tell you really enjoy having sex with me. Oh fuck, oh baby, oh shit."

I blushed. "I'm glad you enjoyed it, Oliver. I'm glad you enjoyed me!"

We just snuggled together, kissing, cuddling, making small talk. "Maria?"

"Yes, Oliver?"

"I have to go. I have to catch an early morning flight to meet my wife in Florida today. I don't want you to think this was all some elaborate ruse on my part to get into your panties."

"Oliver don't be silly. I certainly wasn't expecting you to spend the night."

"I wish I could, I truly wish I could spend the rest of the night, cumming with each other, enjoying each other."

Oliver stood up and began to slowly get dressed. "Oliver."

"Yes, Maria?"

"I have a present for you. I want you to video what I'm about to do."

Oliver looked at me quizzically but pulled out his phone and began to video me. I lay back on the bed and began to rub my stocking-covered legs the way he had. Then I started to scoop up the cum dripping out of my ass. I brought it to my lips and was drinking it from my hand and licking my hand clean. I began to finger fuck my ass, using his jizz as lubrication. First one finger, then two, then three.

"Mmmmmm, Oliver. This is your cum inside me. I'm pretending these fingers are your cock fucking me. I love your cock inside me Oliver. You fuck so good." I started licking my lips while I rubbed my nylons and fingered my ass. The sight of Oliver videoing me, the feeling of me masturbating while he watched was quickly bringing me to the edge again.

I began to cum and was screaming, "Fuck me, Oliver. Fuck this pussy. You're making me cum, Oliver. It's you making me cum! Aaaaaaahhhhhhhhh! Mmmmmmmmmmm!" My eyes rolled back in my head, I was licking my lips and fingering myself furiously. When my orgasm subsided, I looked up at Oliver.

He was standing there stunned, just staring at me. "Just a little going away present, Oliver. It sounds like you won't be having sex with your wife so if you need to cum this weekend, you can go into the bathroom and watch this video while you jerk off to me, imagining yourself fucking me again and again."

Oliver finished getting dressed, I watched him from the bed. He walked over, leaned down, kissed me passionately and said, "Thank you, Maria. Thank you for the kindness I didn't deserve. Thank you for just listening to me. And thank you for that incredible video. I'm sure I'll masturbate to it more than once while I'm in Florida." Then he walked out the door.

....

In the morning, I called Ken and told him about last night's events. "Wow. I'm glad it turned out that way. I just wanted him to apologize and realize what an asshole he'd been. It sounds like he's re-examining himself and his actions. Sounds like we won't have to leave the company after all."

....

The company had always gotten Christmas bonuses. Standard form letter supposedly from Mr. Ross with our bonus announcement. This year, I got double the normal bonus with a handwritten letter from Oliver. "Dear Maria, Please accept this extra bonus for the life lessons you gave me. Also, I want you to know that I deleted the video you made for me. In the same way you allowed me to shred my letter to you, I deleted that video. It doesn't exist anymore. Besides, I've got it memorized! 😉 Thank you for everything you've done for me and for the company. Oliver Ross"

....

Ken also got a handwritten letter with an extra bonus although his bonus wasn't quite as generous as mine!