Halloween reminds me of one of the sexiest, most erotic times I had, even though it didn't occur on Halloween, though. It did involve masks, though.
While I was away on business in Chicago, I had to go to a masquerade ball. The dress code for the ball was black tie & gloves but no full face masks. I dressed up in a tux with a black Carnival mask & driving gloves & went to the hotel ballroom.
There were plenty of women there with hot bodies. As far as looks went, you really couldn't tell much with the masks on but my eyes trained on one lady in particular. She was tall with a tight, aerobicized figure & a very slinky backless pink gown with elbow length black silk gloves. This lady definitely had her A game going. I went over & spoke to her when she went towards the bar. Her name was Lina. It turned out that she was a personal trainer (athletic women: my biggest weakness). She was in town like me for a couple of days & even though she had to make an appearence at the party like I had to, she really wanted to let loose for the night & have fun.
After a lot of drinks & some very suggestive slow dancing on the dance floor, we retired to a corner booth & ordered a bottle of champagne. About a third of the way through the bottle, hands were exploring each others' anatomy & we were making out heavily. I was getting extremely worked up. "We need to take this to a more private area", I said. I didn't yet know how freaky she was. Otherwise, I was willing to take her in a corner & have sex with her right there. We decided to go up to my room. We took our champagne bottle & snuck out of the ballroom, content that we had been there long enough to have said that we were there.
As we got into the elevator, we started making out again. As we were the only ones in the elevator, she started undoing my bow tie & shirt. By the time we made it out of the elevator, my shirt was already completely unbuttoned & out of my pants. We staggered to my room (we still had on our masks & gloves), took out the key card, slipped it in, & opened the door. I held it open while she took the champagne bottle, went inside, & turned on the light. It was then that I decided to fulfill an erotic fantasy that I'd had for years.
She walked over to the window while I closed the door. "Oh, what a nice view", she said as she looked out the window. I was up on the 40th floor. There were some office buildings across the street that still had people in them working, since it was only around 9 or so. I quickly stripped out of my clothes, keeping my mask & gloves on, & walked up behind her. I started caressing her body & kissing her neck. She softly moaned as she cocked her head & our lips met. My hands slipped her gown off her shoulder while my tongue explored the inner regions of her mouth.
Still wearing her mask, Lina started to remove mine. "No", I said. "Let's keep them & the gloves on". She smiled a wicked smile & started kissing me again. I bend down behind her & slid her thong off of her hips with my teeth, while she still faced the window, while still kepping her sexy black stiletto heels on. She gasped but I didn't know why until I got back up. When I stood up, there were two ladies in one of the office windows across the way staring at our window.
Lina could've moved away from the window or pulled the curtain, since it was right next to her. Instead, she stared right back at them. Seeing this, I decided to raise the stakes. I started kissing her again & let my hands roam all over her body. Her nipples were pointed & hard from her excitement. I moved my left hand down to her pussy. It was dripping wet. I started to rub it.
Lina broke off her kiss & started to moan as she turned her head to face the office workers across the way. As I stuck two fingers in (with my gloves still on), she started grinding her hips. She threw her hands up against the window as she started fucking my fingers, grinding in a rhythmic motion. She started moving faster & faster as my left hand matched her movement while my right hand wrapped itself around her hip, keeping her close to my body so that she could also feel my hard cock against her. Her body tightened up as she screamed & came.
Now, it was my turn. I turned her around to face me & started kissing her again. Suddenly, I grabbed her legs underneath her ass, lifted her up, & put her against the glass, those sexy stilettos still firmly attached to her feet. As she started wrapping her legs around my waist, I spread her legs a little & guided my cock inside her. She took it eagerly, thrusting herself towards me while I put it inside her. She decided on the tempo, moving her hips & fucking me, even though she was the one pressed against the glass. I matched her ferociousness thrust for thrust, both of us cursing like sailors the entire time. It was some of the dirtiest, nastiest sex talk I had ever done up to that point. Her muscles tensed with each thrust, while the feeling of her silk laden hands grabbing my back felt so erotic while the wearing of the masks only added to the eroticness of our scenerio.
As I kept fucking her with wild abandon, I glanced over to see if the ladies were still watching. They were, although I was surprised that they weren't playing with themselves. Maybe it was where they were at in the office. Maybe it was because they were watching together. I was getting more turned on by the fact that they were watching & started fucking Lina even harder. I decided after a while (after she came 2 more times) to finally let go & came deep inside her pussy, slamming her against the glass with each thrust while I shot load after load of hot cum. It was at that point that we took off our masks & kissed deeply. I took off my gloves while she kept hers on as we went over to the bed, finally.
I hoped that the ladies enjoyed their show but that was all they were going to get that night. We weren't done fucking, though. It got more erotic as the night went on. I'll share those stories at a later point.
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