3 comments/ 29162 views/ 16 favorites Taking a Chance By: gracesnowpaw Taking a chance – Online fun leads to real encounter Note: This story contains adultery and pregnancy risk content intended as fantasy entertainment. It wasn't long after signing up for a 3D social website for adults when someone introduced themselves to her. As she watched the animated avatar on the screen swaying sensually back and forth she read the pop up. Twisted: Hi there, nice avatar Grace: Hi, where are you? A dark haired male character walked in front of her and waved; floating over his avatars head was the name Twisted. Twisted: You must be new? Grace: Yeah, I just joined. Twisted: Let me show you around. For the next couple hours Twisted toured her around and explained how to find her way around the site and all the crazy actions that could be performed. When Twisted mentioned that the avatars could have sex, Grace was intrigued. Twisted took the opportunity to talk about her darkest fantasies. Grace was reluctant at first and after hearing his fantasy, she decided to open up and share hers. The safety of anonymity allowed her to speak freely and let her most inner fantasies come out as she wrote. Grace: Don't judge me! Twisted: I would never. Grace: I have a fantasy of being taken against my will. Twisted: Nice. Like date raped? Grace: Yeah, I guess. I fantasize that I meet a guy and then he takes things further than I anticipated. No matter how much I beg, he takes me. Twisted: That is so hot Grace. I would love to play that out with you. It didn't take long before their two avatars were naked and playing out a date fantasy that ends up in her begging him not to cum in her, but he fills her pussy up with his cum. The play was so freeing that she found herself aroused and needed to take care of herself after she logged off. Months went by where Grace would regularly log in when her husband was away or at work and Twisted was always there to get her juices flowing. It wasn't long after the first time that she found herself masturbating while they played out different variations of her dirty fantasies that always resulted in Twisted shooting his load in her avatar. Little by little the two of them shared small details about their real lives and descriptions of one another. Twisted described himself as a tall French Canadian man with a big thick cock; Grace described herself next. Grace: I'm 5'4 and 100lbs with red hair. 34-25-36 Twisted: Nice! I love red heads Their online relationship moved to them sharing real pictures of themselves. Grace sent a faceless body picture of herself on vacation for Twisted. Twisted sent a picture of a huge hard cock protruding from a tall slender man. This definitely fueled their next play session as she could envision his body and cock as they played. On a typical training course for her employer, she found herself alone in her hotel room and logged in. It was only a few minutes when her playmate logged in and said hello. Twisted: How's my girl tonight? Grace: Bored, alone in this big hotel room Twisted: Work sent you away again? Grace: Yeah, stuck in freaking Ottawa Twisted: Seriously? Grace: Yup. Twisted: I live in Ottawa. Grace's heart raced and her mind kept the pace. Had she gone too far and told him too much? She had been looking forward to her normal play but things got real quickly. She couldn't actually meet him could she? Twisted: We should go grab a drink Grace: I'm married Twisted: A drink Grace: I don't know Twisted: We can meet somewhere mutual and public Twisted was very convincing and she knew she was going against her better judgement when she climbed in a cab and it pulled away heading to the bar where he had suggested they meet. Instantly upon her entering the bar, a tall dark haired man smiled and made his way to the door to greet her. "Twisted?" Her heart was racing as she extended a nervous hand out to him. The stranger ignored her hand and gave her a friendly hug, "Yeah, but my mom named me Will." Sitting across from each other in the booth, Will put her at ease with his relaxed and friendly demeanor. Will openly flirted with her and repeatedly complimented her on her looks and how much he loved ginger haired girls. Grace couldn't help but love the attention and the danger of being out with a stranger. As the drinks flowed, she found herself flirting back with him. Occasionally they danced and Willy took some liberties as he grinded himself against her. She enjoyed the attention and her mind kept flashing back to all the fantasies they had played out. This man knew all her dirty secrets, all the things she could never let her husband know in fear of judgement. A slow song started and they made their way to the dance floor. Will pulled her close and she felt his lips on side of her head. His big hand turned her face up and he kissed her causing her to remain there in shock as his tongue pushed in to her mouth. Holding her head he continued to kiss her and the guilt was slowly replaced with excitement. Butterflies attacked her stomach and she couldn't recall feeling so alive. When she began kissing him back, his hands wandered down her back and rested on her ass cheeks. She couldn't help but enjoy the attention; her marriage was very loving but sex had become very repetitive. The evening flew past and without warning the lights were turned on indicating it was time to leave. Standing in the cool night air Will held her close and looked down at her. "What happens now?" "We each go home and log in to finish this date?" She smiled at him. "Really?" He raised an eyebrow. "I was hoping to get my cock sucked." Grace swallowed hard as she fought with the idea. She would love to see that cock in person but she just couldn't do it; it would be too far. Will took her hand and began walking for the parking lot. "Come with me, I'll drive you back to your hotel." Grace knew he wouldn't take no for an answer. After opening the passenger side of the truck for her he climbed in and closed the door. As the cabin light faded, Will reached over and pulled her face to his kissing her. "You have me so fucking horny Grace." Willy sat back and unzipped his pants quickly exposing his semi erect cock. As he held it in one hand he looked at her with begging eyes. "Please baby, just a blow job." His big hand massaged the back of her head and she found herself leaning over. Grabbing his hard cock her mind raced, flipping back and forth about getting caught and how his cock was so much bigger than she had imagined from the picture. His cock pulsed in her hand and she slowly opened her mouth letting his cock slide gently between her lips. Willy began driving causing Grace to attempt to sit up but Willy's hand guided her face back down where it belonged and she succumbed to her oral fixation. Sucking his cock deep in her mouth, she teased her tongue around it. She struggled with the lack of access the position put her in and did her best to try and get his cock to explode before the console wore a hole in her side. Bringing the truck to a stop, Willy removed his hand from her head and she sat up. They were in her hotel parking lot. Willy popped his seat belt and put his cock back in his pants, "Let's finish this upstairs." Grace watched as he walked around the truck and opened the door before offering his hand to help her out. He was a perfect gentleman and portrayed himself accurately in the fantasy world. Her heart raced as they made their way through the lobby and up the elevator. Taking her key, he opened the door to her room and let her step past him before entering and locking the door behind him. When their eyes met, Grace could see the burning look in his eyes and the need for her to finish what she started in the truck. She kneeled and slowly pulled his pants down over his hips allowing his rigid manhood to pop free in the air. The hard cock rubbed the side of her face causing Willy to moan as she helped hip step free of his pants. "No underwear eh?" Grace giggled devilishly as she looked up at him. Willy put both hands on her head and guided her mouth back to his cock, "Shut up and suck this." Grace sucked and licked his hard cock feverishly. Free from the awkward position in his truck and full access to his manhood pleased her immensely. She was determined to give him the best blow job of his life. Willy's hips slowly fucking in and out of her mouth as he tried to work his big cock down her throat. Grace gagged and her eyes began to water causing her to look up and meet Willy's gaze. Willy smiled at her, "You lied! What happened to no gag reflex?" He continued to fuck her face faster now. Grace waited in anticipation for him to erupt in her mouth. Holding her head tight, it was clear that she was no longer in control as she gasped and gagged at the big cock pounding at the opening of her throat. Vast quantities of drool coated her lips and face as he tried to work his big pole down her throat. She listened for signs of his impending orgasm but it wasn't to be. After what seemed to Grace as an eternity, he released her head and she panted trying to catch her breath, "You need to cum. I can't take much more of this." "I need to see you naked. Take your clothes off." Willy pulled her to her feet and began undressing her making sure that she knew it wasn't really a request. Once naked, he pawed at her delicate white flesh and sucked each nipple in turn as he sat on the edge of the bed. When he had finished tasting her, he guided her back between his legs to his drool laden cock. As she sucked he squeezed her breasts and she purred with pleasure. She was finally in control again and didn't have this cock forcing its way down her throat. Willy seemed to be permanently on the brink of orgasm, but it never happened. Clearly she was going to work for this and he was holding back to savor the moment. Putting his hands under her armpits he hoisted her face to his and kissed her. As they kissed, he pulled and teased at her nipple with one hand while the other buried three fingers in her wetness causing her to gasp. His fingers expertly pushed in and out of her causing her heart to race and the ever familiar beginnings of orgasmic pleasure. He was focused and on a mission, similar to the one Grace was on with his big cock, but clearly she would have to wait as her body began to convulse wildly. His hand never slowed causing her to chew her lip in an effort to regain control. Willy finally relinquished his grasp on her pleasure source and stood up. Before Grace could aim his cock to her mouth, Willy lifted her up catching the back of her knees in his elbows. He held her there hoisted in mid-air unable to move before slowly lowering her to the point his cock rubbed her backside. "Ready to get bred?" Grace's eyes widened in horror, "Willy that is all fantasy! Please put me down." Willy wiggled Graces petite frame and his cock found the opening to her wet pussy. It danced wildly across her lips causing her to gasp and moan uncontrollably. "Willy please! No!" Lowering her down, she was impaled by his rock hard cock. Screaming out as the weight of her body worked against her; pushing more than she could handle in. Willy licked and sucked at one of her nipples as he bounced her up and down on his cock. It was only moment and his big balls slapped against her ass "Oh god please, no more. I want to suck it." Grace pleaded pointlessly in to his ear. His actions told her that he was going to use her like a fuck toy whether she liked it or not. His cock pounded her deeply and she felt as though she may split in two. Standing in the middle of the room Willy smiled wildly at her as he bounced her roughly on his cock. The pleasure her tight pussy brought him needed to last as long as possible. It was getting more difficult with every thrust though. His heart pounded and his cock stiffened as he looked in to her eyes. The mix of pleasure and horror on her face was more than he could take. "Take my cum you little slut!" Willy screamed out as he pounded her harder than before. Grace's eyes widened, "No please. Don't. I'm not..." She could feel his cock pumping its treasure in her. "I'm not on anything you asshole." Once he was sure that his cock was drained he lifted her off him and set her down wobbly legged in front of him. "That was so fucking hot Grace." Cum ran down her thigh, "I told you to stop." "I know that made it even hotter." Willy squeezed her breasts. "What if I got pregnant?" Grace's face was concerned. Willy laughed wildly, "I'll have my own Grace I guess won't I?" This was everything she had ever fantasized about. Willy had played it out perfectly for her. Grace contemplated the situation as she stood dripping in front of the man who just seeded her, the stranger who was not her husband. Guilt took over her as she realized she wanted more. Willy was slowly gathering his clothes and getting dressed. Grace watched as he tucked his softening cock in his pants before zipping them up. "Where are you going?" He was surprised at her words and raised his eyebrow. "I believe in the fantasy, you keep me hostage and use me all night long." Grace gave an evil grin as she climbed on to the bed on her hands and knees. Taking a Chance 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. "Okay." 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. "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." "Odd." "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. "Exactly." "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 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, 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. "Wow." "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. Taking a Chance After a couple of minutes of this, she pushed me off, and flipped over on all fours, showing me her ass and looking over her shoulder suggestively. I contemplated her ass and dripping pussy, pondering the squishiness of her bed and how to position for traction, which had been a bit difficult even in missionary. "Come on stud, fuck me like you're mad at me!" she nearly yelled, and I suddenly got an inspiration. Jumping off the bed, I pulled her ass to the edge of the bed, and, standing behind her, entered her pussy hard and drilling. She screamed what sounded like mostly pleasure, and I pulled her hips back on to me, pushing in every single millimeter of my dick that I could stuff into her tight pussy. She screamed even louder, and I slowed, concerned, crying out "Was that too much? Are you okay?" "FUCK DON'T STOP!!" came her reply, so I resumed pumping her for all I was worth. She started crying out with each thrust, grunting loudly, as I pounded her with literally all my energy. I was beginning to fatigue a bit, but I wanted to ensure before I slowed at all that I got this girl off, and just as I was starting to consider slowing she moaned "Oh fuck, I'm almost there! Don't stop!!" I took a deep breath and kept it up, and after about six or seven more hard strokes, felt her pussy clamp hard on me as she started to tremble hard with her whole body, actually convulsing. "Fuck me!" she let out, breathing hard while bracing herself, and as she moved forward a bit, I slid out. She semi-collapsed on the bed, then quickly picked herself up, turned around, and looked at my cock. "Oh no, that won't do. You can't make a girl cum like that and not nut yourself." She pulled me to the bed, guiding me on to my back, then quickly straddled me. I groaned as she began riding me like she was on a horse she was trying to break. "Don't worry about me," she admonished, "you've already got me to pop twice. This is all for you." And with that, she pushed her drooling snatch down to my balls, and I felt my internal temperature rise a bit more. My arms and abs burned from the recent activity, but she pulled my head up to her tits and I forgot about that as I eagerly sucked one, then the other, into my mouth. We got in a good rhythm, and even though I felt ready to cum, it didn't immediately rush forth. Pretty soon, she started breathing a bit ragged, and kissed me, murmuring into my mouth "You're determined to fuck me stupid, aren't you?" I sat up a bit more, pulling her into me as I began pushing down on her hips as she slammed down. "I'm determined to fuck you into oblivion," I growled. She slowly started panting, and, hoping to get one more cum out of her, I wrapped one arm around her back and waist, pulling her into me, as I put my thumb on her clit and drilled her for all I was worth. My hunch paid off, as she began breathing hard enough to hyperventilate, and let out a mighty, growling "Ahhhh fuckkkkkkkking HELLLLLLLLLL!!" As I felt her clamp down, it pushed me over the edge, and I released what felt like a river of cum out of my now sore cock, grunting like some sort of wild dog. She steadied herself against me as I collapsed back on the bed, and she fell forward on to me, kissing me again, playing her tongue into my mouth as she slowly calmed. She pushed up a couple of inches, exhaling, and muttered a long, satisfied "Goddamn. Thank you." "Thank you," I happily responded. "No, seriously, thank you. I haven't been fucked like that in a long time. All the cute ones in this town are either intimidated, want to act like they're you're boyfriend, or have barely any stamina. I needed that something awful." She pushed back slightly onto my flagging but still rather hard cock. "You're still hard," she slightly moaned. "Any chance of a rematch?" I started to wonder what kind of a crazy nympho I had picked up. "Yes, although I'll need a bit of a breather first," I chuckled. "Of course. Me too. You plowed me nice and sore there," she said with appreciation, as she slowly slid off to the side. "I wasn't trying to hurt you." "I wasn't complaining, hot stuff." "Okay." She kissed me again, absentmindedly tracing her fingers on my chest. "Shower?" I nodded, and she led me by the hand into the bathroom. We got under the hot spray, washing each other playfully, her paying special attention to my half-mast member, even playfully sucking on it a bit, before getting out and toweling off. I felt some stirrings, and didn't want her to stop, but truthfully knew I probably needed a little more rest first. "Come on, I'll give you a tour of the rest of the house," she said, and she led me down the stairs, us both still as naked as babies. I wasn't shy, and she certainly seemed naturally at ease, so I shrugged it off as her eccentricity. She led me down to the downstairs, showing me a little gaming area, guest room, etc, as we passed all kinds of photos I hadn't notice before. Besides what were obviously family and childhood shots, there were dozens of shots of her with scads of good looking girls and guys that looked like they should have been in hollywood flicks, even just as extras—toned bods, attractive faces, the whole gambit. I thought one or two looked slightly familiar, but shrugged it off. She continued the tour, bringing me into a huge home office filled with computers and what I instantly recognized as video editing equipment. "You do video?" She turned around with an expression of shock. "How'd you know that?" she asked. "You have video editing equipment. I work for a Public Relations firm, and I do a lot of video editing for our clients' Youtube and Vimeo channels." She seemed to consider me for a moment, and then slowly nodded "Yes. I run a production company that does a lot of web video. You might have seen some of our work, even if you don't know our name off hand." I was about to ask her about this, when she walked into a next door room, switched on the light, and illuminated what looked like a movie set, with several computers, cameras, and lights all pointing to a bed with a big cloth backdrop hanging behind it. And it all clicked. "That kind of video." "Well, not as much myself anymore. I do shoot scenes for my flicks in my house sometimes, in a pinch. But nowadays I only appear in a handful of scenes a year. I started my own production company four years ago and mostly produce nowadays." Holy shit. I had just fucked a porn star. "So Tiffany?" "Is my real name. Roxy Danger on film." "Wow." I was a bit floored. "You okay?" she inquired, trying to read my face. "Yeah. Fine. just a bit surprised, is all." "Okay. Some guys get a bit weird when they find out. If you want to leave I'll be more than willing to drive you back or grab you a cab." I read some nervousness in her face, the first of the evening, which surprised me a bit. I thought of her bent over, getting drilled on camera, and to my surprise, I realized my cock was hardening. I had an overwhelming urge to pick her up and fuck her even rougher than before, right there in the doorway of the makeshift studio. I checked myself for a second, silently wondering if this was normal, my reaction? I knew the situation definitely wasn't. "So can I ask you a question?" I broached. "Sure." "How many people have you fucked on camera? Or even overall?" "Seriously?" she shook her head. "I have no idea. How about you?" "Overall, 42. I went through a slut phase in college. Or at least I thought it was one," I added sheepishly. "So you're okay?" she said, sauntering toward me, her head tilted to the side. "Yeah. A tiny bit surprised, but I'm fine. Honestly, as long as you fuck me again like that, I'm good." She put her hands around my neck, kissing me deeply, then reacted as she felt my stiffening cock. "Oh damn..." she trailed off, reaching down and fondling my steeling prick. "You are going to be trouble, aren't you?" I pressed my tongue to hers, as she broke free and said "I like trouble," leaning in again as I grabbed her tight little ass. "Come on, I'll show you my equipment," she said, leading me back into the office. She led me to a wraparound desk with a bunch of monitors mounted to the wall. I was in geek heaven as she sat me down in an office chair, then scooted up a second beside me. She clicked on a few folders, and brought up some windows. A few videos popped up, and a video of a cute by rather stick-ish blonde popped up. "This is something I'm working on for our next release. It's a typical blowjob compilation." And as she pressed play, the blonde walked forward, dropped to her knees, and began pulling open the fly of some guy who apparently had a monster cock, but no face. She smiled a stupid grin and began deep throating him like it was nothing. Tiffany quickly demoed a couple of her controls and edited a few crappy frames out. Then, without any real warning, she set the movie going again while leaning over to take my engorged prick deep into her mouth. I sighed as she engulfed me for a few seconds. "So tell me, is she your thing?" she inquired. "Not really," I responded, as she slowly and deliberately stroked my cock with her hand. "I prefer a curvier woman." "How curvy?" she asked, as she pulled up a whole bunch of thumbnails. They enlarged slightly as she moused over them, and a few, I noticed, were women that were likely in excess of 350 pounds. "Not that curvy," I called out. "Okay, how about this?" and she quickly came into women that were a bit in what would probably be termed the MILF category, with fuller hips and big, natural breasts, but still some hourglass to their shape. "Much better," I responded, as she engulfed my cock again. "I see you approve," she smiled, pulling off for a second. "Sorry if I scared you with the big girls there. Everybody has a different kink, you know?" I nodded, enjoying the sensation of her blow job. "Do you have any shots of you?" I asked, curious. "I haven't shot in 6 months at least, so I'd have to dig in archives. You really want to see me fuck somebody else?" "Well, I was more curious what you look like done up for the camera," I confessed. "I worked in a strip bar in college for about a year, and I was just curious what you looked like done up, since the film girls I met generally put on a ton of makeup, so much that you wouldn't recognize them on the street if you saw them." "That's kind of the point," she replied. "Hang on," she said, navigating to some folders of stills. "Here." An image of a very done up girl with big hair and a snake wrapped around her shoulders popped up. I laughed. I could tell it was her, but she was so heavily made up that it was difficult. "I know, I know..." she giggled, gripping my cock more firmly as she slowly pumped me. I was starting to get really turned on, and considered suggesting a trip back to the bedroom, when she brought up some more videos of the aforementioned curvy women, and as she hit play, she said "This is something we just filmed. A series on girls with big natural breasts" A very buxom and incredibly sexy redhead filled the screen, doing a little preliminary striptease. "I so wanted to fuck this girl, but she had a boyfriend. Otherwise I think I could have." Her breath was getting a bit ragged again, and I could tell this was really turning her on. She sat down on my lap, and began fast forwarding the controls a bit, as she slowly, almost agonizingly began to draw her very moist slit over my hard dick. I started to move my hips a bit unconsciously as the girl on camera began sucking a cock, giving what looked to be a very good BJ with tons of spit and eye contact. "This was her first ever movie. She's going to be a natural," she said breathily, as I reached around and started to gently massage her clit. We continued like this for a couple of minutes, me gradually increasing my pressure and speed, as she slid her now liberally lubing pussy up and down my shaft. On screen, the girl had just climbed on to the guy's pole, slowly putting it inside her, as Tiffany began to really rock back against me. My cock was coming dangerously close to her entrance, but I didn't care, the rational part of my brain that said "Hey, condom!" was slowly becoming quieter. After a few more strokes with her pussy, she arched back far enough that my cock sprang free from under her pussy, and as she came back down, I felt the warm wetness of her tentatively engulf my tip. I wanted to stop it. I tried to say something, but feeling her body over me was amazing, and as I raise up my torso a bit, gravity took her 2/3 of the way down my shaft. "Ohhh. God that's nice," she purred. "Fuck..." was all the reply I could manage. I knew I should pull out. Knew it. But I couldn't, she felt too good. I tried to grab at her hips as I straightened up fully in the chair, but she used the opportunity to grind down on to me, enveloping me in her warm, velvety cunt. She grabbed on to the arms of the chair, and began using them as leverage to fuck me in a fluid, yet firm motion. "Oh fuck that's so good," she said. "Your cock is so nice." as she started to push down into me with some firmness to her strokes. Onscreen, the redhead had been moved into doggy, her cute, sexy mouth hanging open as her tits began swaying from the hard fucking she was getting. I began really pumping into her with some energy. "You like her?" she asked, as I pushed my cock into her wonderfully wet, tight hole. "Yes. She's fucking hot as hell." "Hang around me for a bit, maybe I'll introduce you," she offered, as she tightened her pussy around me. Gone as I was, buried in her, I still knew not to overcommit when I was balls-deep in another girl, no matter how open-minded she obviously was. "I'd like that," I said, "but only if I can keep fucking you for a very long time." "You'd better," came her reply, as she ground down hard into me. We were starting to pick up speed. "We shouldn't be doing this like this," she said, as I felt her push her back against my chest, pulling on my legs to get me deeper into her. "I know. You want to get up off me and I'll put a condom on?" "In a bit," she moaned, "I can't bear to pull you out of me yet." We kept on. I knew it wasn't a good idea, but I was so fucking turned on. It'd been years since I'd fucked a girl bareback, since even when I was with my ex-wife, she had gone off the pill because she didn't like the extra pounds in contributed (personally, I'd loved how it had added a tiny bit to her hips and greatly plumped up her titties). The crazy, primal nature of this fuck was just intoxicating, and I didn't want to break it. Finally, I was determined to do the right thing, and I grabbed her around her waist with one hand, lifting with my legs while keeping my hard prick firmly lodged in her cunt. She was reasonably light, so it wasn't horribly difficult, but the added gravity and force just caused me to penetrate her even deeper, and she cried out and said "Oh fuck, yes! Dammit baby, you've got me so close." Her legs went slack, and I felt her feet brush the floor, so I decided that instead of breaking the moment, I'd bend her over the desk and keep going for a bit. In that moment, I felt her body absolutely melt to me, and I swear it felt like our hips were joined as one. I shook my head to clear it, but the feeling was impossible to shake. I started my previous trick of slamming her as I pulled her hips back on to me, and she grunted with appreciation as we fell into another gear of carnal rutting. I was pumping in and out of her with abandon, but wanted more than anything to push her over the edge, so I reached around and cupped her breast, toying with her nipple, as she began cooing with appreciation. After a few more moments, I brought my arm back around her waist, and started to pull her back while i reached with the other and spanked her clit. A few seconds of this, and my hunch paid off big time, as her pussy contracted and she squealed a mighty "Ohh fuuuuccckkkk yesss!" I heard a splat, and looked down to see some fluid falling from her cunt to the plastic chair mat we were standing on. I held still and grabbed on to her to keep her steady as she convulsed with her orgasm. She swayed slightly as her legs gave way, and I kept her upright, although my cock partially dislodged so only the head was still impaling her. She steadied herself against the desk, catching her breath, and then looked back at me. "Don't move," she admonished, and I watched her lift her leg up, swinging it over my head as she turned her torso over and around meticulously, supporting her weight with her arms as she kept the head of my cock trapped in her pussy. I nearly lost my load right there, I was so turned on. She pushed back against the desk with her arms, and I slid forward back into her molten, heavenly slit. I leaned her butt against the desk as we resumed our previous pace. "We shouldn't be doing this," she said again, though the tone in her voice was wanton and didn't speak of any desire for me to pull out. Everything in my mind screamed at me to stop and use protection. But I was so in the moment, I couldn't even comprehend the idea of pulling out. Still, I offered weakly, "Do you want me to stop?" "Fuck no!" she yelled. "You feel so fucking good I don't want you to ever stop!" "Good. Me either," I panted out, as I began pushing into her even more vigorously. I knew I was a ways away from cumming anyway. "Just don't cum in me," she blurted out. "Don't worry," I grunted, "I don't want to knock you up." "Fuck that, I'm on the pill. But how long since you've been tested?" she asked, slowing her pace, as the concern and logic started to finally start to overrun the logic part of one of our brains, thank god. I sensed the seriousness of her worry, and stopped my hips to speak to her and put her at ease. "About six weeks ago was my last STD test. I was getting regular checks because I was worried my ex had been cheating on me. We were using condoms as birth control, but I needed to be sure, so I've been doing it monthly for the past nine months." "You've had sex since her?" "Yes. But only with protection. I haven't fucked anybody bareback for over 3 years until tonight." With that, she pulled me in again, and we resumed our previous pistoning. "Fuck it. Cum in me if you'd like, I'm game. Just don't stop fucking me." And with that, she stuck her tongue into my mouth, as she leaned backward and opened up her legs to take me in more. I pushed in as far as I could manage, as she wrapped her legs around me. Then, all of the sudden, I heard a creak that sounded ominous. We froze, as we both looked down at the desk. "Glass desk. Bad idea." she spat out, and I nodded. "Where then?" I asked, somewhat urgently. "Couch!" she indicated, nodding her head to one across the room somewhat urgently. I picked her up, and walked her quickly over to the couch, setting her down as I more or less fell on top of her and bottomed out. She pushed me in farther as I continued to we resumed our pace again, this time with her pulling me in insistently with her legs and snaking her hands up around my shoulder blades. We were both beginning to sweat profusely, which in the dry desert air is an accomplishment. As she started arcing her pelvis up to me in an attempt to get even more of me into her, I could feel the approach of what felt like her getting close. I knew I didn't have a ton left in me, as I was tiring a bit due to our frenetic pace, and I was so turned on I was likely to erupt in a bit regardless. "You gonna cum for me soon, baby?" I asked. "Uh huh," she moaned, biting her bottom lip, and I put a little more pop into my hips as I thrust downward. A few more strokes, and I was rewarded with a crescendo of moans and grunts as she began to shake with a mighty "Hoooollllyyyy FUCK!!" Her pussy creamed a bit more, and as I pushed in a few more strokes, I tried to clench my butt muscles to hold off at least one more minute. Taking a Chance Tiffany, it seemed, had other plans. As she began to get her wits about her again, she pushed mightighly with her cunt, gripping me firmly, and said clearly in a low sexy tone, "Fucking fill my cunt with your cum, you fucker." That was all it took, for some reason that dirty talk sent me over the edge, as I felt my own release shoot forth with a power and force I had never felt before. My vision tunneled down to the smallest point of light, and I steadied myself as my balls emptied so many times that I lost count. "Holy shit!" she laughed, "I'm glad I wasn't trying to swallow all of that!" I dropped to my elbows, and as my equilibrium returned, she reached up and kissed me again. "Fuck!" she exclaimed. "Yeah," I agreed. "That was something." We laid together for a few minutes, her still minorly grinding at my slowly deflating dick. "That," she said, "wasn't just something. That was amazing." "Yeah," I said again, all I could muster. My dick finally softening, I lay beside her. We laid in silence for a few minutes absentmindedly touching each other. "Do you have to go anywhere in the morning?" she inquired sweetly. "No, it's Saturday. I don't have anything going on." "Okay. Would you like to stay the night. Maybe get breakfast tomorrow? We can go get your car in the morning, but I'd like to hang out a bit more. Maybe have some more fun?" "I'd like that," I said. I chuckled. "What?" she asked "What a bizarre evening," I said, shaking my head. "I suppose," she said, "but I thought it was pretty fucking fantastic." "Oh, yes, absolutely," I replied. "beyond amazing. It's just not what I expected at all." There was a pregnant pause, and I could tell she wanted to ask something. "What?" I asked. "Are you sure you're okay with this? With what I do? I mean, I was just thinking this would be a quick fuck, and you'd run away screaming and scared when you found out more about me. But you didn't..." "Why the fuck would I..." I interrupted, but she held her hand up. "Let me finish," she said. "I need to get this out." I nodded, and she composed herself, sitting up and placing her hands on her knees. Despite the fact that she looked freshly fucked, I noticed that she had a very businesslike air to her, and I suppressed a smile at the contrast of her naked, sweaty, cum-drenched form and her demeanor. "Here's the thing. I kind of like you. You have a brain, and you didn't run or pass judgement when you found out about what I do. I'd like to see you some more, and have some fun. But while this was fucking great, don't get me wrong, I'm not a normal chick. I don't believe in monogamy in the fucking slightest, nor do I want to be tied down, but if you fuck somebody else besides me, you bet your sweet ass you're going to use protection. But I do want someone to hang out with, go places, enjoy the company of, and have all kinds of crazy, wild sex with. So I present you with your choice. If you don't think you can handle a girl like me, then we should probably just say 'hey, thanks, it was great,' call it a night, and wish each other well. But if you think you can deal with a cool girl that's also a cock-crazy nympho, who will suck you off and fuck you in public at the drop of a hat, might occasionally fuck another guy for fun, or even a bit of money, but will also try to get you laid by any other gorgeous girl or two, and might even join in if I'm inclined, that's the type of girl I am. I'm also kind of a pain in the ass, I'm pushy, have been called domineering, and I have expensive tastes. I'm right a lot, sarcastic, rude, impatient, passionate, impulsive, and I've been told I'm just a bit crazy. That's who I am, what I offer, and at this point in life, I'm too stubborn and old to change. Take me or leave me." I looked at her long and steady. She seemed calm, but just a touch bit nervous under the surface. I rolled it around in my head for a bit, pausing to consider the pros and cons, and I knew my answer almost immediately. I paused for another second for dramatic effect, finally deciding I'd made her squirm enough. "So my favorite breakfast spot is on Central. It's called 'The Breakfast Club,' and the food is amazing. Plus I kind of like the fact that they have some majorly cute waitresses in essentially tight yoga pants. We can ogle them while we eat. And it's not to far from where I left my car, so we can get that after we eat, and then do whatever. Sound good?" Instead of answering me, Tiffany pounced on top of me, pinning me to the couch and grinding her still sodden crotch into me as she attacked my mouth. "I'm going to need another minute before we go again," I cautioned. "Maybe some food and a shower, too." "I can get you up," she countered, giggling, pushing down into my member. "I'm sure you can. But I still need food and a bit of cleanup first," I countered. "Yeah, I do too," she said, smiling. "Okay. Food. Then cleanup. Then you're mine." And with that, she sprang up off the couch, grabbing my hand as she guided me back downstairs toward the kitchen.