Taking a Chance

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Authors note: this is based on some actual events from years ago. Obviously, I’ve changed details to protect me and added to make a better story. I’m considering making it a series. Enjoy, and please leave feedback.


“Yeah, I guess I just wasn’t a fan,” she said.

“Of what? The weather? Hills? People, food?” I asked.

“All of it, really. San Francisco just isn’t my speed.”

“Huh. Well, obviously, being from there, I do kind of like the city,” I responded.


Another uncomfortable silence hit, at least the fifth one of the night. This date was definitely a bit crappy. I turned and looked toward the bar, wondering if I should order another drink to distract myself, or just close out my tab, make an excuse, and leave. We’d only been here for maybe 30 minutes at the max, and though it was just a first date, it wasn’t going great.

Perhaps I should back up. A few months earlier, I’d gotten divorced, and, hoping for a fresh start in life, I moved to Phoenix, taking a job one of my buddies had been hinting at wanting me at for years now. I’d met this girl, Connie, on an online dating site, which I’d joined because I was tired of the girls I met at bars and yoga classes, the two main places I went where women frequented. While she’d seemed nice over messenger, the photo she had sent was well over 10 years old, and we seemed to have absolutely nothing in common. We didn’t like any of the same music (literally), she seemed to adore the trashy reality tv and fluff entertainment I despise, there was at least 15 years separating us, she wasn’t my physical type, and while I tend to be studious and at least a bit sarcastic and humorous, she was, to be frank, a bit shallow and her sense of humor seemed lacking at best. I couldn’t think of two people who had less in common than we did, and while I certainly wasn’t looking for anything serious at the moment, I seriously felt zero spark with this woman. I asked myself if I was just being overly picky, or principled, but shrugged it off and realized that nothing about her turned me on, minus a reasonably cute face and absolutely gigantic breasts, which were amply displayed.

Mercifully, then, her phone went off. She glanced down, then announced “It’s my babysitter. I need to take this,” as I indicated I understood. I looked at the bartender, who was giving me a look of sympathy, having no doubt heard our awkward banter, and indicated that I would be right back. I started toward the rest room, plotting my exit strategy as I went.

It was then that I saw her. Raven black hair, striking blue eyes. Small, slender, but with a very generous amount of curve on her frame. I could see a few tattoos on her, peeking out from underneath her top, along with a tiny stud in her nose and a piercing in her eyebrow. Two words went through my mind. Bad Girl. Cliche, I know, but still, I knew I had to meet this woman. As I walked by, she glanced over and made eye contact with me, and a sly smile played around the corners of her mouth. I considered stopping, but instead went to the restroom and did my business. I glanced in the mirror, and did a quick gut check. Now, I stand decently tall at 6′ even, with a slimmer, decently toned bod, brown hair, green eyes, and I know I’m relatively good looking, but I’ve never been the classic pretty boy, nor have girls ever flocked to me. But a few months from my 30th, I could still pass for a college kid, and as I splashed a little water on my face after washing up, I had the feeling that I was playing with house money tonight, so what the fuck, right?

On the way back, I glanced at the front, noticing Connie still on the phone. I saw the back of the head of my object of lust, considered a few different approaches momentarily, and quickly trashed them all, figuring what the hell, I’m already on a shitty date, what’s one more rejection at worst? So, with little fanfare, I sat down in the booth on the same side as her, and just launched in headlong.

“Hi. My name’s Martin. Sorry to barge in, but I’m currently on one of the worst dates of my life, I saw you, and I wanted to at least talk to an attractive girl before going home and cursing my night. How’s your night going.”

The look on her face was a bit shocked, as I could tell men didn’t often approach her like this, but then it muted and changed to amusement. She tilted back a bit, extended her hand, and said “Hi Martin. I’m Tiffany. This is my friend Marsha.” I shook her hand, lingering a moment but not too pervy, and then gave Marsha a quick shake as well. Marsha was cute, in that blonde, I’m trying to look like a California beach babe even though there is no beach nearby way, but Tiffany was the real head-turner for me. “So,” she continued, “what’s so bad about your date?”

“Oh, nothing monumental,” I shot back. “She’s very nice. She’s just about 15 years older than me, and she’s kind of a country and disco listening, church-going kind of gal. And I’m the exact opposite.”

“Is that so?” she asked, staring directly into my eyes, and I could tell she was evaluating me. I knew my next play had to be right.

“Yes, I’m afraid so.” I paused, maintaining eye contact. escort kartal “Anyway, I was planning on calling it a night on my date soon, but after I walk her to her car, I’d like to come back and buy you a drink. Both of you, that is.” I watched them exchange a meaningful glance.

“Yes, I think I’d like that,” Tiffany replied. “Go do the polite thing, and hurry back if you can. Nice to meet you, Martin.”

I nodded my head, and set out on my mission. Fortunately, when I got back up to the bar, Connie was already on her way back in, hanging up her phone. “I have to run, I’m sorry. The babysitter is having trouble getting Emma to sleep. Maybe we can do this again sometime?”

“No problem,” I told her, as I signaled the bartender to close out my tab, and signed my receipt. “Let me walk you to your car.”

I opened the door for her, chatting amiably as we made our way down the block, until she stopped next to a beige Toyota. “This is me.”

“OK. Well, good luck with the babysitter and the baby, and thanks for coming out to meet me tonight.”

“Martin. Listen. I think we had a slightly rocky first date, which was mostly on me, I was distracted and my head is in a weird place tonight. Maybe I can make it up to you sometime?” And before I could answer, she swarmed in, hugged me closely, and gave me a very sweet peck on the lips. What the hell?

“Yes, I’d like that,” I responded, secretly a bit bewildered.

“Good. I’ll call you.” And with that, she got in her car, started it, and drove off, waving as she went. I stood there confused for a minute, but then shrugged it off, going back toward the bar, taking special care to remove all traces of lip gloss she left behind.

When I arrived back in, I was pleased to see my object of lust was still there, and casually sat down beside her. “I have taken care of all other obligations this evening, ladies, and am free to socialize with you now,” I said, affecting a stuffy air.

“Gee, thanks,” Tiffany shot back sarcastically. “You’re in a good mood for somebody who just let a woman down,” she said, arching an eyebrow.

“Actually, I’m under the impression she may want another one. Apparently we were on different dates.”


“Tell me about it.”

“Well either she thinks you’re cute, or she’s just had so many shitty dates lately that you’re an improvement,” she noted.

“So it’s either my physical appearance or the fact that the bar has been set incredibly low for her that is getting me in her good graces?” I asked.


“Not my witty repartee or cynical charm?”

“Nope,” she shot back. I noticed Marsha wincing while she tried to suppress a giggle.

“Well, I’ve been called worse things than a bimbo fishing in the lower expectations pond, I suppose.” They both burst out laughing. Score one for me.

“Touche, bud, touche,” she laughed, shaking her head. And with that, I had a feeling I had her attention, and the banter just started. She dragged a good deal of information out about me, but I noticed that she was very reserved about certain topics, for instance, only saying she was part owner of a film production company, but was very effusive on music, food, and even politics and religion, which she actively brought up. She seemed fiery, and I really, really wanted to see how far that extended.

About this time, Marsha made her excuses, and begged off for the night. When hugging her friend goodbye, the two of them shared a conspiratorial whisper, and then giggle, and I knew they were talking about me. I was hoping my chances of getting some had just increased. “Say, I’m also considering getting out of here. Do you want to help me walk Marsha to her car?” I agreed, paid the bill, and walked discreetly behind them as they chatted. Marsha said her goodbyes again, then drove away. Tiffany turned, looked at me, pulled me to her by the belt, then abruptly kissed me, roughly and passionately, grinding her body into me. I liked where this was going.

“So,” she said, “you seem to have no shortage of confidence, but do you really think you can handle me?” Before I could answer, she grabbed me and stuck her tongue deep into my mouth again.

“Well,” I responded, catching my breath, “I’m hoping so, but I’m sure that either way, it’ll be fun to find out.”

“Gorgeous,” she said, “you’re pretty, but you have no idea.” And with that, she said “Come on.”

“Where we heading?” I asked, playing dumb.

“My place. You can follow me, or ride with me, if you don’t mind being my captive.”

“Take me away,” I joked, simulating handcuffs. She looked down at my wrists and smiled.

“That gives me a fun idea for later,” she smiled, leading me by the hand. As she turned, her mane whipped around in the slight summer breeze, and I realized I was already excited.

She led me to a late model Corvette, and as she got ready to back out, she reached over and kissed me again with incredible passion. I suddenly was very glad I’d put condoms in my pocket before leaving. She backed out, and sped off, pinning me against the seat with g-force. I grinned over at her. “It takes about 20 minutes to get to my place. I’m maltepe escort thinking if I speed a bit, that’s less time until you’re bending me over.” I felt myself tent in my pants, and as she shifted, I felt her hand slide over my half erect cock. “Not bad. Definitely has potential, presuming you know how to handle it.” And with that, she stared at me with a questioning glance. Instead of trying to banter back and saying something boastful and borderline douchey, I just started back at her, half smiling. Needing to look at the freeway as we merged on, she was the first to blink, looking back, but I thought I noticed her cool demeanor get a tiny bit rattled.

We drove in mostly silence, her speeding, cornering the car crazily, occasionally reaching over and giving my leg, torso, or cock a quick squeeze. I touched her a bit, but didn’t want to push too much since she was driving—and a bit recklessly, at that. Finally, after getting off the freeway and taking a few quick turns, we pulled down a residential street with some very nice houses. She clicked a garage remote, and swung left into a very large garage. I noticed a BMW, a newer pickup, and a motorcycle in the garage as we got out. “Do you have roommates?” I inquired somewhat nonchalantly.

“No, the cars are all mine. The Vette is a great toy, but not that practical for everyday driving.” She led me into the house, and we passed into an impressive yet understated living room. “Do you want another drink?” she called out, crossing into a dining room, then another sitting room, past a gigantic TV and entertainment center, then over to a built-in bar.

“No thanks, I’m good,” I said, still a bit awestruck by the house. I was leasing a 2 bedroom condo, and considered myself to be doing quite well for a 20-something fresh off a divorce. How did this girl afford all this?

“Okay, but I’m going to have a whiskey. Hope you don’t mind.” I shook my head and smiled. “Want something non-alcoholic?” She rattled off several options, and I chose a diet cola. As she sashayed over to me, she looked at me quizzically, obviously wondering why my jaw was open.

“Compared to a lot of my buddies, I thought I was doing well, but I think i’m in the wrong business, looking around here,” I remarked, sipping my soda.

“Well, if it consoles you, only a handful of people can do what I do. She took a healthy swig of her whiskey, then grabbed the back of my head, kissing me roughly again. I savored the taste of her mouth, and as she came up for air, she exhaled and moaned a soft little “Mmmmm.” She backed off, refilled her glass, and beckoned “Follow me.” We went out to the back patio, which was enclosed in screening, and she reached out for a light remote, turning on some underwater lights that illuminated a very nice pool. She another swig, nearly draining her glass, and glanced over at me. “Fancy a swim?” Her words slurred a tiny bit, and her upper body flushed a bit. It was a warm night, still being September, and I was game to let her set the pace, as I really didn’t believe there was a chance I wasn’t getting laid at that point.

“But I have no suit,” I mock objected. She was already pulling off her pants, including her underwear. I noticed her nice toned legs, and though I couldn’t see her ass from this perspective, as she stepped out of them, I got a small peek at a nice, pretty pair of pussy lips, shaved completely bare.

“Bah, mine’s upstairs, I’m not walking all the way up there to get it. Just strip down.” And with that, she started to take her top off, and I quickly moved to catch up. As I whipped my shirt off, I saw her breasts swing free, and as I stood captivated for a split second (they were nice, perky, D-cup or close to it at least, with large, pink nipples the size of at least silver dollar pieces) she flung her bra right in my face. “Tag!” she yelled out, and ran through the door. I quickly followed, shucking my last sock and diving after her. She swam away from me, and I kicked toward her, eventually catching her. She turned over onto her back, doing a half backstroke as she coaxed me with her onto a little stoop, motioning me to sit beside her. I did, and quickly she reached over, straddling me as she kissed me, fingers of one hand running through my hair as she trailed her fingers along my chest, playing them over my nipple, then slowly working down. I ran my hands over her back, reaching down with one to cup her ass, which was delightfully firm yet with just the right amount of squish. Slowly, she worked her hand down to my cock, which was now at full attention, gripping it firmly and slowly pumping it. I moved my hand to the front and began to lightly toy with her lips, brushing her clit ever so gently. She grinned evilly at me, and said “Swimming always makes me horny.” As she stroked me, I slowly wiggled a finger into her, and she groaned with appreciation as I began slowly playing it in and out of her, moving towards the G-spot. “I like that.”

She tilted to pull me out, and then pushed backward to put her body back in the pool, steadying herself and then sucking my hard member into her mouth. I pondered that she must have done this a few times, pendik escort bayan as smooth as the movement was, which oddly, turned me on even more. I moaned audibly as she quickly swallowed all of my length with abandon.

While I’d had what I considered a decent amount of experience, the gradual realization that I was going to bed a girl who probably had a ton of sex didn’t make me uneasy, it only excited me. I wanted to make her cum so much that she’d want me on the regular—a good looking girl, great in bed, with a pad that would make anyone jealous—what wasn’t to like?

Just then, a light came on, and as I turned, I realized it came from the neighbors’ yard. She popped off, putting her finger to her lips to signal silence. I nodded, and she led me off the stoop, swimming as silently as we could. She stooped low, and as we got back to the patio, she killed the light in the pool, then reached in the darkness to hand me a towel. We silently patted dry, and she reached over and kissed me again, grabbing my cock and leading me back into the house by it. When we got in, she said “I hate when the neighbor guy spies on me. He’s watched me there with a couple of guys. Pervert. Besides, it’s fun to play in the pool, but you can only really fuck with abandon when it’s the wee hours, and not on that stoop. I vote for our first time in my bed.” She kissed me, then led me upstairs, past a couple of rooms that were darkened yet open, and into a decently impressive master bedroom. She turned on and dimmed the lights to halfway, then walked to the bed, sat down, stared at me, and patted it. I came over, and she said “Where was I? Oh, yes…” and began sucking me into her mouth while I was still standing.

She was amazing, working a perfect alteration with a bit of figure 8 with the mouth, her full lips trailing longingly, then moving to long, full tongue licks, all the while keeping almost perfect eye contact with her deep, blue-green eyes. I was in heaven, but I really didn’t want to just stand there while this girl sucked me into oblivion, which I knew was a possibility if I let her keep going too much longer.

I pushed her off, picking her legs up and swinging her to the edge of the bed, and I kneeled before her pussy, which I noticed was positively dripping. “I have to warn you, it takes a whole lot of eating to get me to cum,” she playfully teased.

“Good. I love a challenge.” And with that, I dove in, slowly licking around her lips, completely avoiding her clit. I kissed the inside of her thighs, coming near, but deliberately keeping away from her sensitive button, feeling her anticipation build. She resumed playing with my hair, trailing her fingers over my neck and shoulders, and as I noticed her forearms starting to tense, I figured I had teased her enough and dove in to her clit before she could pull me inward. I started lapping eagerly, taking my tongue from soft to firm, teasing from different directions until I figured out what seemed to make her moan the hardest, a simple side to side stroke with a medium firm tongue.

Her breath began to get ragged as I slowly resumed my G-spot routine from the pool, and then after a bit, on a hunch, I pulled her clit in between my lips and sucked lightly. That finally did it, as I felt her pussy clamp down on my finger and her legs began to shake as she let out a gradual “Ohhh…ohh…ohhhhhhhhhhh my FUCKING GODDDDD!!” She clamped her legs, pulling me into her pussy and momentarily smothering me in her cooch, then pushing me off as I tried to resume my attention. “No. Please. No more. That was amazing, but after I cum I’m hyper sensitive.” I nodded my understanding as she caught her breath. She ran to her bathroom, grabbed a glass of water, and returned, downing part of it, before handing it to me. I started to wave it off, but she pushed it into my face saying “Least I can do, you earned it.” I smiled, took it from her, and as I was drinking, she dropped to her knees and began sucking me into her mouth again, before reaching into her nightstand. I watched her smoothly take out a condom, unwrap it, and using her mouth, she slowly put it on my dick while blowing me. That, I thought, was definitely a first for me. She crawled up on the bed, rolled over on to her back, and beckoned me to her with her finger as she spread her legs rapidly, swinging them over her head and easily touching the headboard.


“Yes. I’m a contortionist.” Was I dreaming? This was the type of shit that happened in Penthouse letters, not real life, and certainly not to me. “Quit staring and get over here,” she growled.

I snapped back to reality, hurried up onto the bed, kneeling in between her splayed legs, and put the head of my now painfully-swollen cock against her pussy, rubbing it back and forth a couple of times against her clit before deftly sliding it in a couple of inches. I tried to pull back before pushing in slowly, but she reached forward, grabbing my ass with her hands and pushing me in to the root in one rough motion. “Goddamn I love a nice thick cock,” she purred, as I began sawing in and out of her. She pushed back up at me hard, and I took the hint and began pulling her hips into me hard enough to create some impact. “Yeah, give it to me rough,” she said, and I tried to oblige, pushing my cock and hips forward forcefully on each thrust as she began to grunt like some kind of feral beast, which just made me want to fuck her harder.

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