The Meet Up

It was the end of January and by sheer luck a full 24 hours of sunshine had burst through the sky in Toronto melting most of the ice and snow away from the sidewalks, outside of the large black piles stacked up next to the roads from an immense snowstorm less than a week ago. I walked out of my hotel as gingerly as possible in the 4" black, knee-high, stiletto-heeled boots that I had no business wearing regardless of the winter conditions.

"It's only one block," I whispered to myself as I cautiously moved as close to the building as possible in case I suddenly needed to catch myself in mid fall against something. "Damn it. I knew I should have practiced more."

In the back of my head, I was secretly glad I wasn't meeting my boyfriend for dinner. There were way less people on the street at 9 p.m. to gawk at my awkwardness. I also knew that if I could just make it to the barstool at the wine bar and put my butt in it, I'd be okay until the walk home, when I'd have an extra set of hands to guide me.

A cold wind blew up the street and my teeth chattered. The few inches of skin covered only by thigh-high stockings between the top of the boot and my short dress felt the burst of chill the hardest. The ball of my foot ached in the boots. I shook my head. "The things we do for fantasy," I whispered.

A taxi driver pulled up next to me on the sidewalk. He rolled down the passenger window and called out in a heavy African accent, "Need a ride, lady?"

"No, thanks, it's just a few doors down."

"I like your boots," he said smiling. Then he whistled and drove on.

When I reached the door of the wine bar, I felt a little proud of myself. I hadn't broken a shoe or fallen on my ass. I opened the door and felt the heat warm my face. I walked as casually as I could to the row of empty bar stools and took off my conservative black wool coat revealing a very short, very expensive, bright red dress. The lacy tops of my stockings were hidden while I was standing but would be slightly revealed when I sat down. The dress was fitted for someone a little taller and a little leaner than I was, but the back bunched in such a way around a large, solid black zipper that ran from the top of the dress to the very bottom that it did wonderful things to emphasizing my ass. It was the first size 4 dress I'd fit into in my life, and I was more proud of that than I was of making it down the block in the hot boots.

I put the coat on the back of my chair and pulled myself up and onto the stool, crossing my legs delicately and reaching for a drink menu.

The bartender had been behind the bar when I walked in, but I was too focused on getting from point A to point B safely to realize he had been watching my every move. When I looked up from the page to say good evening, he wore a dopey grin on his face that I read as guilt. He'd been caught checking me out.

He was close to my age, mid thirties, around 5'11" tall with dark, overstyled hair. He was of Latino descent with amazing skin, bright white teeth and a build that was nothing but thick muscle underneath a very tight gray t-shirt.

"What can I get you?" he asked quickly putting a napkin down in front of me.

"Blue Moon, please," I answered folding the menu over and pushing it away.

"Yes, Ma'am," he responded reaching for the bottle in the refrigerator under the bar. I looked up at the screen. No surprise: hockey. The Senators were pounding the crap out of the Habs. I watched for a few seconds more before the bottle appeared in front of me.

"You know if this were a Friday or a Saturday, you'd have men all over you in that dress," the bartender said as he popped the cap off the top and reached for a frosted glass.

"Keep the glass," I responded. "The bottle is fine."

"On a Wednesday, though, no one is here to notice, which isn't usually why a woman wears an outfit like that."

I took a sip and raised my blue eyes to meet his brown ones. They were extraordinarily dark but filled with flirtation. I smiled. He smiled back. "Have any special plans tonight," I asked teasing.

"I caught a glimpse at the zipper on the back of your dress when you took off your coat and was hoping you'd let me peel it off of you after my shift," he said.

I blushed and smiled again. "I'm afraid that act is reserved for someone else," I answered.

He nodded and smiled. I reached into the pocket of my coat for a $20 bill.

"Drinks are on me, at least until he gets here," he responded.

"Thank you," I said picking up the bottle and taking a long drink while staring up at the TV again. The Canadiens were starting to make a comeback and the fans in Montreal were going crazy in the stands.

Minutes passed and I got lost in the game. I was halfway done with my beer when I felt a large, determined hand push my brown hair aside before soft lips hit the back of my neck. I bowed my head giving him greater access. His hand moved down from hair to the zipper at the top of my dress. Slowly, inch-by-inch, he gently pulled. When he reached around the area where my bra strap was, I protested and turned to face my lover behind my chair.

"What? Like that's not what it's intended for?" he teased while quickly rezipping the dress, kissing me softly on the lips twice, as a greeting, and resting his right hand on my left thigh possessively as he sat in the stool next to me.

The bartender studied my lover as he took his drink order. Lover is older than I am. He's tall and has an affinity for black work jeans and polo shirts. What's completely amazing about him isn't in his look – which is very normal. It's in his specifics. I adore the way his beard is graying. Every few months the gray slowly overcomes more and more of his curly brown hair, but in the beginning it started at his temples and crept down his sideburns toward his black goatee.

I also love his hands. In his every day profession, he's an artist, mostly drawing and painting and computers. But he also builds with them: carpentry, tile work, etc. He's good with them. The first time he touched me I expected them to be rough and a little worn from his frequent projects, but instead, they were smooth, immaculately clean and much better manicured than my own.

Then there are his eyes. He dismisses them as just being normal blue. But they're not. They're the kind of blue that you notice if you sit on a hillside in the Caribbean observing where the expected greenish water of the shallows hits the slate blue of increasing depths. Those eyes have looked into mine with such heat that my legs weakened in response. They've watched me with an intensity of such examination for so long that years after we'd become intimate, I still don't feel like I have the strength to stare back into them for longer than a few fleeting moments. At the same time, I've seen them turned stormy and frustrated. Once or twice they've put me in my place, but more often I've seen them turn nasty in response to life's annoyances and difficulties.

Lover looked up at the screen and shook his head. "Fucking hockey," he said with a sigh. He was not a fan of sports that took place outside of the bedroom.

"You'll live," I responded picking my beer up again to take a swig with my right hand, while pushing the hand he held on my thigh a bit under my dress. In response to the invitation, Lover closed his eyes and smiled. He was entertained by my audacity.

It had taken me the better part of the afternoon to get over my girl freakout in my hotel room. When I'd first put on the get up, I'd literally smacked myself in the face and then hid my face in my hands. Who knew that dressing sexy would also feel ridiculous and completely unnatural.

"Only three people wear outfits like this in public," I said to myself in the full-length mirror, "One: Cougars looking to get laid. I know it's not supportive of my older, divorced sisters, but it's true. Two: High-priced hookers. And Three: Girlfriends who are happy to indulge their lover's fantasies."

I happened to be number 3, but I felt more like number 2. Julia Roberts at least knew to go cheap. My get up had cost me an insane amount. And in the end, the $400 dress and $300 boots were likely to just end up wadded up on the floor. I wasn't really excited by how I looked in it either. I felt like I was looking at a completely different person. Who was that girl and what, in these particular clothes, did my lover hope to experience?

I had thoughts of just putting on a decent pair of jeans. He would be slightly disappointed if I waited to put on the costume until we were back at the hotel, but he'd understand. So why bother with the costume at all? For me, it wasn't the sex that was the pay off. It was how he'd look at me. The pure enjoyment on his face while watching me do something out of my comfort zone, experiencing a different level of my own sexuality. In short, I liked to play the game. I liked that I had control over how things went. And I liked when I genuinely surprised him.

The bartender had wandered off to serve a table of three that had just arrived in the corner leaving us alone for the moment.

I felt lover's fingers run over the top of my nylons under the skirt. "The tops of your thighs are wonderfully soft," he said just slightly louder than a whisper.

"Tell me what else you like," I said quietly.

"The shoes and the dress are lovely, thank you." He said leaning in closer to me and whispering in my ear. "The make up, the hair..."

"It's like I'm a real girl," I inserted while turning my head to meet his gaze. It made him laugh and his eyes sparkled at me and then turned heated.

"You are most definitely a real girl," he said kissing me softly on the lips.

"How badly do you want to unzip the zipper?" I teased knowing the thought had to be on repeat in his head.

He sat back moving his arms in wide gestures, "It's just there calling out. I mean, can you blame me?"

"No," the bartender interjected. He was pouring drinks behind the counter again eavesdropping. "I told her that on any other night she'd be swarmed by men."

That was all it took. One comment of competition and Lover reached for his wallet to close out the tab. I stood up to put on my coat.

"Happy unzipping," the bartender said to me as he handed Lover his credit card slip to sign.

"Thanks," Lover responded not looking up to recognize the bartender had been speaking to me. I smiled at him in response and turned to make my way to the door. On the street, Lover took my arm through his for some support, and we walked back to the hotel.

Standing in the foyer waiting for the elevator, Lover asked me to take off my coat.

"Why?" I asked.

"Because I want to watch people look at you."

I blushed, but removed my coat and folded it over my arms. A woman walking by snapped her neck around to look at my outfit and ended up running into a pillar in the hallway.

"Nice," Lover laughed. "It's a good thing we got you off the street. You could cause serious accidents."

I shook my head. He was over exaggerating, which I recognized as him paying me compliments, but at the same time embarrassing me.

When we got on the elevator alone, I pushed the 22nd floor and just before the doors shut, the zipper was being moved down my back at a rapid speed.

"A--" I got out the first letter in his name as I turned to toward him. Instantly, his lips were on mine. My hands reached up toward his face, but before they got there, he picked me up and pushed my back against the elevator wall. My legs reacted by wrapping around his lower back. His glorious mouth and experienced hands were everywhere.

"This dress needs to come off," he growled.

"Down boy," I said. "We're almost there."

The elevator dinged and he put me down. The back of the dress was unzipped to my waist. Somehow he'd gotten my bra unclasped in the flurry of handiwork. I moved as quickly as I could down the hall to my room, pulling my key from my coat pocket. Lover's body was pushed up against mine at the door to the point where I could feel his erection hitting my ass through his jeans.

I pushed the key card in, saw the green light turn on and turned the handle on the door. Those were the last three motions where I was in control.

Lover's firm body flattened against mine and shuffled us into the room. I remember hearing the door fall shut just after the zipper was undone completely.

"Surprise, no panties," were the last recognizable words I distinguished as the dress separated in the back and lover's hands slid over my hip bones and then up to my breasts. His lips were at the back of my neck again and his breaths were more of a steady pant. The window in the suite was open to a beautiful view of the city all lit up. A small chaise lounge chair was turned toward the window and a plate of cookies and a small container of milk on ice sat on the table from the turndown service.

Lover maneuvered us over to the chaise, while massaging my breasts and nipping at my neck. When we reached the chaise, his hands slid to my shoulder blades and he pushed the dress and bra entirely off of my body and tossed them onto the seat of the chaise. I turned to him and started unbuttoning his polo shirt. He undid his belt and pants and pulled them off. His stiff cock with its large spongy head poked out from beneath his shirt. He removed his socks, and then I tugged his shirt over his head.

As I reached for the zippers on my boots, he snatched my hands back up. He sunk to his knees, ran his hands up the boots, the outer parts of my thighs, over my ass and then down to my knees, parting them and placing his lips against my clit. I reached backward and grabbed onto the chaise trying to figure out how I was going to not writhe around to the point of falling over in the wicked, hot boots.

His quick pants turned into more of a series of growls as he worked my clit and clutched my thighs. When I was warmed up and plenty wet, he turned me to face the open window and bent me over the back of the chaise. His right hand ran up the back of my thigh, over my ass and onto his cock, which he quickly guided into my pussy. I gasped at the pleasure. He groaned at the sensation and began to pump in and out of me at a confident but consistent rate.

His teeth nipped at my neck again and his right hand pulled gently at my hair. My hand reached down and found my clit. His balls slapped into me aggressively with every plunge. The panting returned and as his penis hardened even more, I began to moan ever so loudly. His hands, which had been in various places positioning and supporting, rolled over my D cup breasts and his fingers played with my nipples roughly. It took three dual tugs before I began to shout.

"Don't stop. I'm coming!"

A lesser lover would have quickened his pace in the excitement, but Lover held steady. Even after the first wave passed, he continued. I asked to change position, since I'm always oversensitive after orgasm, but he didn't relent. He wanted something more from me. A few more strokes in and out of my vagina with his penis and he slowed his pace so he could wet one of his fingers. He started up again, but this time, instead of teasing my nipples, he slid a finger into my ass.

I swore.

And then I came -- hard – sending my ejaculate all over Lover, the floor, the back of the chair. We were drenched in sweat and my cum.

Lover withdrew his dick and pulled me around to the other side of the lounge chair. He pushed my dress to the floor before he lay down on his back and pulled me onto him in a straddle position. As I rode him, I tried not to notice how much attention he paid to my body. He focused on my breasts bobbing up and down, my neckline, my face curled up in the middle of sexual satisfaction.

And this was what I loved most about our relationship. I felt earlier that day that, as a lover, I was giving a lot by dressing up and expanding my comfort boundaries– but in that moment of sexual passion, when he caught my eye and I was able to hold his gaze as he came into me, I was reminded about what an amazingly generous lover he is. Sure, his own orgasm is enjoyable and preferred, but his favorite part about sex, has always been watching me experience pleasure. He took great joy in it. He took greater joy in giving it. It made our relationship reciprocal and highly symbiotic.

I fell forward onto his chest and kissed it. Then I turned my head up and kissed the nape of his neck up to his ear.

"I love you," I whispered rubbing my nose over the gray hair at his sideburn.

His arms wrapped around me and pulled me tighter to him. His lips kissed the side of my face. A sigh of satisfaction escaped his lips. I smiled and closed my eyes letting him hold my body to his.

"So," he whispered, "That was one of my fantasies. Now it's your turn. Name it. It's yours."

See? Amazingly generous...