The Double Dare Hotel

Some guys never learn. Even after you've told them a dozen times or more.

"Hey Boss, ain't that your wife?"

I didn't even look up to check. Bob's sense of humor runs to the obvious and mundane. One of the girls from the architectural firm upstairs probably wore a short skirt today and Bob thought he was being funny or subtle. He was rarely either.

Jill couldn't really be here. Despite the importance of today, she was at work. The medical field is not one to go into when you're looking for lots of time off or the ability to set your own hours. I understood. I wasn't free to set my own hours either, so we would have to celebrate her special day after we both finished our appointed tasks. It had me a little annoyed, but Bob had no way of knowing it. I bit back the mean-spirited comment that first came to mind and went for light-hearted sarcasm.

"Nope, can't be her. C'mon Bob! You know County General is clear on the other side of town. Not enough time to get back and forth to make lunch dates feasible. Must be my girlfriend."

"First I've heard of a girlfriend. Is she cuter than me?" said a sexy voice that certainly did not belong to my balding and rotund assistant.

"Honey? But you had to ...I mean, I didn't expect...What are you doing here?" I left the figures on my screen to appreciate one far more enthralling.

"What, a girl can't get taken out for lunch on her birthday?"

"Well, unless your present was a new car and you changed your mind about the validity of the speed limit, we don't have time for lunch Ten minutes and you're going to have to turn around and get right back on the road. That's barely a cup of coffee."

"Then let's go have a cup of coffee...or something stronger."

I shrugged and smiled up at my wife. The look she returned was odd: a mischievous grin. Just as I wondered what she had up her sleeve, she straightened, and I could see that she didn't have any sleeves. She wasn't wearing her scrubs. I automatically expected to see her in work clothes, and their lack caught me by surprise. Something was definitely going on here.

Instead of asking more questions, I logged off the computer and went to the coat rack to get my suit jacket.

"Hey, Bob?"

"Yeah, boss?"

"I'm gonna go get some lunch. If they call back on that Walker file, tell them I'm in a meeting and I'll give them a call after the market closes."

"Will do, boss."

"Thanks," I said as I walked out of the office and around to meet my lovely wife in the lobby. "I'll see you in a bit." I took Jill's hand and headed out the firm's glass doors into the relative privacy of the city streets, my first goal to ask about the surprising change in attire.

"Now, since when do you bring a change of clothes to the hospital? You were wearing your scrubs when I walked out the door this morning. I'd bet money on it."

"Other people's money, I'm sure. You always play your games with other people's money. But yes, you're right...I was wearing my scrubs. I just felt like getting through lunch without fielding questions about headaches and hangnails. This is actually a new dress. You like?"

"Very much. It just caught me off guard. So, where do you want to eat? Sixth Avenue Bistro?"

"Actually, I just thought we could go for a drink. There." Jill pointed to the Doubletree Hotel across the street. The top floor was a bar with a famous view of the city, a benefit commonly associated with the top floors of thirty story buildings, but it was a very unusual choice for her. Even inside, Jill wasn't exactly fond of heights.

"Okay, why not? I know the manager, I gave him some good advice about getting out of that adjustable rate. He'll bring us up some calamari from the seafood place if I ask him nicely. And you can tell me what was running through your mind when you bought that flimsy little thing. Not that I'm complaining."

The words died on my lips as we stepped out into the windy street. The strong breeze filtering through the concrete canyons slipped beneath the folds of the blue and white sundress and the fabric lifted away, revealing the pale pink of her bare nipple from where I stood looking down.

"Jill, I..."

She put her finger to my lips and leaned forward to whisper, "I'm not wearing any panties either."

She pulled her lips back from my ear and winked, then turned and walked to the corner. It took me a moment to recover and follow. As I did, I found myself watching the curve of her ass under the lightweight dress and trying to decide whether I could tell. I couldn't, but under a dress how would I see the difference?

Walking up behind her, I fought two conflicting urges as the wind blew. The first was to slide my hand beneath the fluttering skirt and find out if she was telling the truth. The second was to keep it smoothed down so it wouldn't fly up. That one surprised me.

With her sweet, lithe figure, pale skin, and the startling contrast of jet black hair and green eyes, Jill always got plenty of attention. I sometimes reveled in the knowledge that, when we went out, every man—and some of the women—looked at me with envy. Jill was always oblivious to it; it was something she grew up with and just considered a part of her. She never played up her looks, never used them to get a better table or to charm the salesperson. I always told myself that I was lucky in more ways than were obvious, and swore that I would never feel a day's jealousy or possessiveness. So why did I feel the desire to hide her skin when she obviously felt comfortable?

Jill reached back and curled her fingers in mine as the light turned green, and we moved across the intersection and into the lobby of the Doubletree. I started to head over to the front desk where Sean was standing, but she pulled me straight through, grasping my hand and motioning to the elevator. She pulled us past the tourists and business travelers and into an amazingly empty elevator. "Don't you want your calamari, baby?" I asked as the doors closed behind us.

Jill turned and hit the top button. "Actually, I have something else in mind."

She stared into my eyes as the elevator lurched upwards. Her hand reached behind her back and the sound of a zipper being pulled reached my disbelieving ears. The shoulder of the dress fell away and I became mesmerized by the sight of Jill's bare breast.

The elevator jerked to a halt and a bell began an insistent ringing.

Jill stepped towards me, moving away from the panel where she had just pushed the stop button.

"You know Debbie? My old roommate?"

"Of course." I was married, not dead. A man was just as unlikely to forget Debbie as he was to forget Jill.

"We made a sort of deal, many years ago. The opposite of giving birthday presents. On my birthday, she gets to dare me to do something. Next month, I'll return the favor."

"And her dare to you was?'

"This."

As she said it, Jill slid the dress off her other shoulder and it fell to the floor. She hadn't been lying about the panties. For just a moment, she looked uncomfortable, embarrassed. Then she was in my arms and my back was against the wall, my mouth against hers. As the hard points of Jill's nipples rubbed against me through the cotton of my shirt, her hands dropped and started fumbling with the buckle of my belt.

My hands slid down her smooth back to take an ass cheek in each palm and squeeze. As I did so, the belt buckle came open. Jill jerked down on my zipper, and thrust her hand in to slide away my boxers. My hands left her ass to pull the clasp apart and as the fly parted, her hands pulled down on the gray wool slacks.

All sense of propriety fled my mind. I held Jill's thighs in my hands, and spun into the corner of the elevator. I lifted her off the floor and rested her ass against the cold metal of the handrail that encircled the wall and leaned in. As the tip of my hard cock came to rest against the warm wetness of her pussy, the need to fill her overwhelmed me. I pushed up, and she parted to accept my invasion—her pussy already soaking wet. Her hands grabbed at my hair as I continued to kiss her and her tongue hungrily sought out mine.

I thrust up hard and Jill's mouth left mine to gasp lungfuls of air. She let it out in low moaning breaths as I pounded her bare ass against the metal and felt of the elevator wall.

I thrust as deep as possible, pinning her against the corner. I rotated my hips, grinding into her pussy, using almost bruising force. The pitch of Jill's moan rose and her breathing quickened. I pulled back to slam into her and drive her against the wall and grind again. Her mouth found my neck as her legs locked behind my back. As she came, her teeth buried themselves in my flesh and a muffled scream of pleasure emerged.

When the shivers in her spine subsided, Jill threw her head back and stared into my eyes.

"Your turn, honey.... and there is only one way we won't leave a mess. Put me down."

I did as I was told, and she circled to push me back against the corner. She went to her knees in front of me and looked up with the brilliant green of her eyes.

"Come for me, baby. I'm going to bury your cock in the back of my throat, and I want to feel it spurt. I want to feel the warmth of it, want to go through the rest of my day knowing how I did this to you and swallowed your come. Can you come for me, my love?"

"Fuck, woman, I can barely hold back right now. Put my cock in your mouth and it won't be but a minute."

Her eyes never left mine as she slipped her lips over the head. She ran her tongue across the bottom of the shaft, then stared at me as she took the rest of my hard cock into her mouth and throat. Jill made a sound of delight and the vibration sent shivers of pleasure through me. Then she closed her eyes, wrapped her slender fingers around the base of my shaft and began to move.

As my cock slid in and out of her beautiful mouth, my words proved prophetic. In moments, I felt my legs start to shake and my knees get weak. I wrapped my hands in her hair and fought the urge to pull her head down as the first pulse ran through me. Jill gave an unintelligible sound as the first splash hit the inside of her mouth. Her hand continued to pump on my shaft as she milked the fluid from me. As my eyes closed and my shoulders relaxed, I felt her swallow one last time and then slip my cock from her mouth. Gently, she tucked it back into the boxers and slacks, fastened the one button, then left it to me to finish as she calmly retrieved her dress.

"Oh my God, Jill! That was incredible. But one thing I don't understand."

"Yeah, baby?"

"How do you intend to prove this happened—that you really did it?"

"Oh, that part's easy. Debbie has a new boyfriend. His name is Sean, and I think you mentioned something about getting him to bring up some calamari. Honey, come on now! Didn't you notice that the alarm bell had already stopped? Do you really think a hotel like this doesn't have cameras in the elevators?"