Gregs Road Trip

The dark room with the well-lit stage smelled of smoke and echoed with the French accents of Montrealers. The pair made their way through the fuming cigarettes and indistinguishable chatter to a table in a quiet corner. In well-tailored suits amidst the jean and t-shirt-clad men, the two looked slightly out of place.

Scott Greg and Jack O'Donnell had been out all night, but they still had some catching up to do. The two had been roommates in Law School, Jack taking a job with a prestigious international firm in Montreal while Scott joined a smaller, but still well-regarded, firm on the East Coast. They chose a table where they could talk above the din and loud music, but where they still had an unimpeded view of the stage.

"Sexe Excellente" was one of the best strip clubs in the city, frequented by the Habs and Expos before they moved to Washington. The strippers were the best dancers and the most beautiful women from around the world. Most made thousands of dollars a night, drove expensive cars, and took in all the culture the city had to offer.

Scott was attending some boring seminars on corporate governance developments, a recent nuisance thanks to the fallout from Enron. Jack was more than happy to meet up with his old buddy to show him what Montreal had to offer.

"So what do you think?" Jack asked as Scott stared dumbstruck at the stage. A beautiful Latin woman in lingerie was slowly stripping to Britney Spears' "Slave for You." "Hey," Jack snapped his fingers to get Scott's attention.

"She's amazing Jack, the women in this town are something else." He reluctantly tore his gaze away from the stripper and faced Jack.

"Haven't you hooked some gold digger out East yet? I thought for sure you'd snag someone, good job and all."

"No, I haven't met anyone yet. No time with the gym, work and all that, you know how it is."

"Fuck no!" Jack replied, "Man, that's what you said all through school. You were too busy. Relax man, get fucking laid already."

"Oh yeah, I can get laid Jack, I just want, you know, someone to settle down with that's all. What about you, who's this Carolyna chick?"

"You'll meet her when we have dinner tomorrow. She's a dream man, half-Spanish, half-Irish, an amazing body. The girl has great curves and that beautiful tan skin. She's Catholic, mum and dad will love that, and she's fucking smart man. She's a CFA working for the provincial pension plan, she's absolutely loaded. I know it sounds retarded, but it was like love at first sight."

"Wicked buddy, cheers," the two tinked beer bottles as Scott's eyes were drawn back to the stage. The latin dancer, now largely naked, had completed her set and had headed off. As he was about to turn back to Jack, the next dancer took to the stage.

A gorgeous, ebony woman will long, straight black hair strode confidently on stage. With a full, curvaceous figure she presented an incredibly sexy silhouette. Her full breasts pressed together in a tight corset created an amazing amount of cleavage. Thigh-high boots, fishnet stockings, and a whip finished off her costume, apparently she was a dominatrix tonight. To Scott, she looked like a fantasy pin up girl.

Jack noticed his friend's distraction and turned to watch the show. The East Coast was a beautiful place to live, but the women were a little more "relaxed" in their appearance than those in Montreal. This was true for the everyday woman and not less so for the professionals working this club. As far as variety was concerned, the East Coast was largely devoid of the immigration from the West Indies, Middle East, Latin America, and Asia. Montreal was full of exotic and beautiful women from around the world, and they all tended to develop a sexy French accent to boot.

"What's the matter Scott, never seen a black woman before?"

"Funny Jack, funny. I have a thing for outfits and stuff man, fuck off." Scott replied defensively. Jack just laughed it off.

"Messieurs, c'est Mistress Caramel pour votre plaisir et torture!" The DJ announced to the crowd. A group of drunken guys roared, obviously on a bachelor party as one man was noticeably drunker than the rest and wearing a dress. "Qui shall be her next victem?" The man asked, mispronouncing the English with his heavy French accent.

Hands on hips, Ms. Caramel gazed around the room, briefly making eye contact with Scott. His heart skipped a beat as her beautiful brown eyes settled on him. With a quick batting of her long eyelashes, she turned to eye the rowdy group. She took note of the well-dressed man in the corner, but she had a job to take care of first.

The group surrounding the groom-to-be practically threw their friend onstage. He stumbled to his feet in front of Ms. Caramel as she gently took his face in her hand. He was completely and thoroughly drunk. Careful not to break her long fingernails, she squeezed the man's cheeks in so he stood slack jawed in front of her, slightly grinning.

Pulling the man back down to his knees by his face, she set him in a kneeling position and pulled the dress up over his back. His boxer-clad ass now exposed to the crowd, his friends laughed harder and screamed at Ms. Caramel to spank him. In standard strip club fare, the man was stripped, spanked, and generally humiliated in the best way possible, by a gorgeous, sexy woman.

"Now that's what I call a bachelor party, eh Scott?" Jack yelled patting Scott on the shoulder to get his attention. Scott broke away from scene on stage, realizing he'd been staring and licking his lips like a dog eying dinner.

"Yeah, she's pretty hot." He tried to sound nonchalant.

"You should get a dance with her."

"What?" Scott asked, still glancing back as Ms. Caramel gave the man a big kiss before throwing him off the stage into the arms of his buddies. Lucky bastard, he thought to himself.

"A lap dance you idiot. It is a strip club you know."

"I don't know man, isn't that a little sleazy?" Scott wasn't even looking at Jack. He was staring as the dancer made her way off stage and headed towards the bar. Her beautiful round ass swaying from side to side as she walked. Did they teach that at a school or something?

"We're in a strip club Scott, this isn't Sunday School. Here, stay here." Jack rose and made for the bar himself.

"Come on man, don't worry about it."

"Relax, I'm getting a beer, you want one?"

"Yeah, get me a Bud." The next dancer had already begun her set and was gyrating to the dance music. I see you baby, shaking that ass! Appropriate song thought Scott, she did have a nice ass.

"Hello," a sultry voice poured into his ear like honey and brought Scott's eyes to his left. His eyes were greeted with two ample, caramel breasts.

"Up here sweetie." Ms. Caramel smirked as she used one finger under Scott's chin to bring his gaze to her eyes. "Let's go." She took Scott's hand and led him towards the secluded booths at the back of the club.

Rising with a massive grin on his face, Scott passed Jack at the bar grabbing his bottle of Bud and nodding to his friend. Jack winked at him and turned his attention back to a petite blonde stripper sitting at the bar.

Turning to smile at Scott, Ms. Caramel realized he was actually taller and broader than she thought. He easily towered over her and eagerly followed her into the closest booth. Sitting on the bench, Scott put down his beer as she pulled the curtain closed to provide some privacy.

"I suppose I have Jack to thank for this." Scott assumed his friend had arranged this.

"Who?" She replied.

"Jack, my buddy, the other guy in the suit?" She did not have a knowing look on her face so Scott dropped it. "Well, how does this work?"

"Well, I dance and you pay. You can touch my breasts, my ass, but you can't touch my pussy. Got it?"

"Yeah, I don't think I should touch you."

"You're not from around here are you?" She asked, with a distinct lack of a French accent.

"No, I'm from the coast. You don't sound French yourselllffff..." Scott's voice trailed off as Ms. Caramel began to grind her beautiful round ass against his crotch. Scott had had a hard on since Ms. Caramel had taken the stage and she took note of it now as she felt his manhood against the smooth skin of her bare ass.

Giggling slightly, she reached around her back and grabbed his erection, clearly evident through the thin dress pants. "You're so hard, how big is your cock?" She turned and began stroking him roughly. Leaning forward, her breasts hung low before Scott's eyes.

"Seven inch..., what? Okay, I don't get to a lot of strip clubs, but this cannot be surprising. Every guy here must have a hard on." Scott tried to catch his breath. This naughty woman was now giving him a hand job. Could this be happening? Strippers only do this in porno's, not real life.

"I saw you staring at me when I walked on stage," she said, her pouty lips just inches from his. "Do you want to kiss me?"

"I, uh, I didn't think they allowed that?" Scott replied, trying to catch his breath.

"I never said you were allowed, I asked if you wanted to." Ms. Caramel increased the tempo of her fist, beginning to pound away on Scott's cock. She'd teased hundreds of guys this way, and this particular guy looked like he was going to cum in his pants. Scott's hormones were racing and it was all he could do not to grab this woman and ravage her. "Answer me boy, do you want to kiss me?" He couldn't hold back any longer...

"Yes!" Scott gasped. Taking her by her long hair (and completely by surprise), he pulled her to his lips. Instinctively, she slapped him hard across the face, but she was not strong enough to tear herself away. As they kissed passionately Scott plunged his tongue into her mouth. Ms. Caramel tried several more slaps, each more reluctant than the last. Soon, she fell into his arms and embraced him as they took turns thrusting their tongues into each others' mouths.

Pulling her to him with one hand he reached down and grabbed her ass with the other. His biting into her lower lip gave her a chance to let out a muffled moan. Nothing out of the ordinary for the back room of a place like this, moans, kisses, the slap of skin on skin. The bouncers did nothing to intercede.

Mistress Caramel had handled drunk white men before. She had worked at the club for a year now. Graduating with an MBA from McGill, but without knowing French, her prospects in the city were limited. She stumbled onto the place on a lark thanks to an acquaintance. The money was good, but the men were a toss up. Some were assholes who should've been home with their wives and others were like Scott; single guys just looking to cap off a night on the town by seeing some naked women. She thought she'd tease the cute young guy and get a nice tip, he was well dressed and staring at her like a school boy crushing on a cheerleader. Horny boys are quickly parted with their money in places like this, and she'd had her fair share.

She had misjudged this guy though. He looked harmless enough, cute guy, clean cut. His passion and strength had surprised her, she hadn't fully resisted, she was looking forward to teasing him. Now he had pulled down her corset and was biting on her ample breasts.

"Ow, stop! Please, I'll call the bouncers" She threatened him, but in a hushed tone. Scott, mad with lust for this ebony goddess turned and sat her on the bench. Pulling down his pants, he revealed his rock hard cock. Ms. Caramel stared at the pre-cum soaked head of his cock, startled that he had taken it this far.

"Suck it," Scott commanded as he pulled her to the head of his dick. She looked up at him with her beautiful, bedroom eyes. Her lips, especially the lower one he just bit, we red, swollen, and moist. She took his cock in one hand, the dark skin of her fingers contrasting with his rigid white cock. The erotic sight caused Scott's cock to twitch up and run across those beautiful lips.

Tasting the salty pre-cum on her tongue, she gave in to this man's desires and took him slowly in her mouth. Lightly kissing and licking the head, she gazed up at Scott. He glared down at here, her lips puffing out to take his cock into her mouth. She looked so hot.

"Mmmmmmmm," she hummed onto his dick as it pistoned in and out of her mouth. Holding the hair out of her eyes with his hand, Scott proceeded to gently thrust his cock into her mouth every time she withdrew it. Her long fingernails on one hand dug into his ass as the other tried to hold the base of his twitching cock.

"Oh yeah, suck it. Oh Mistress, those beautiful lips feel so good on my dick. You look so naughty with my big white cock in your mouth. Ohh!" He gazed down as he got the best blowjob of his life.

The exotic and erotic site below him was too much for Scott. Mistress Caramel was working wonders on his dick and it had been a month since he'd gotten laid. Never had a woman sucked his cock like this before.

"Oh god, you dirty bitch. Suck that cock, fuck I'm, I'm... Ungh!!!! Yes! Ohhhh" His orgasm had snuck up on him much as his abrupt advances had on Ms. Caramel. He came violently and without warning in her mouth. A month's worth of Scott's cum erupted into her mouth in thick torrents. Shocked at the copious amount of cum spurting into her, she tried to swallow it all right away. But Scott kept coming and she quickly found herself gagging on his cock and cum. His seed spilled out of the sides of her mouth dripping from her chin to her breasts.

"Oh god, Ohhhh" Scott gently cradled Ms. Caramel's head in his arms. She let his slippery, and now softening cock, slide from her mouth and caught her breath. Sitting there, cum and saliva all over her face, she couldn't decide whether to fuck Scott or to get the bouncers to kick the shit out of him. Many clients had tried before, but none had taken her as Scott had just done. She knew she had let him, and it felt so good to give in to his demands.

As the momentary high of his orgasm passed, it finally donned on Scott that he had basically just raped the woman's mouth. What had he done? She started it, didn't she? He started to panic.

"Oh my god." Scott went down on one knee, undoing his tie, he quickly began wiping up his cum that now covered her breasts. "I'm so sorry, I'm a little drunk, I don't know what came over me. Oh god, are you alright?"

So, she hadn't completely misjudged this guy after all. A little hornier and a lot stronger than she imagined, sure, but he didn't seem dangerous. And he did have a nice cock. Now he was trying to clean her up? An idiot for sure, but not an asshole.

"I think I'm alright sweetie." She had spent many a night slapping men around and had quite taken to her role as Mistress Caramel. No man had ever taken her like this, using her mouth for his pleasure. She could feel her wet pussy, she'd gotten off submitting to this stronger, younger man.

"How old are you?" She asked.

"Twenty-six." Scott answered, still worried he'd just sexually assaulted her. He was a lawyer, he knew the consequences and he'd seen enough movies on jail to know he didn't want to end up behind bars.

"Oh god, you're just a boy. You are a horny little bastard though, aren't you? God, you almost choked me with cum." She stood before him, looking down. His cock was hard as a rock again, black socks on, his shirt undone, what a mess. "Take off your clothes."

"Pardon?" Scott was not sure he had heard her correctly.

"Strip, you look like an idiot. Socks on, come on! You can't fuck me like that." The grin on her face put Scott's mind at ease as he peeled off the remaining bits of clothing he had on.

"Now, you came, it's my turn." She sat on the bench and pointed to the floor directly in front of her. "Kneel, good boy. Now, be a better boy and lick my pussy." She slid her panties down off her legs and grabbed Scott by the back of his head.

Realizing he wasn't fucked and he might actually get to fuck, Scott dove into Ms. Caramel's pussy. She had obviously enjoyed being his little bitch as her pussy was already wet. Her long fingernails ran through the short hair on the back of his head, gently pressing him to her.

"Fuck me with your finger, fuck me!" she ordered and Scott inserted his middle finger into her wetness. Stroking her, he played with her G-spot while licking her pussy lips. Her cum was gushing over his face as she began to grind herself into him.

"Ohhh, that's nice. Good boy, you like my chocolate pussy don't you?"

"MMmmmm," is all Scott could do to reply as his tongue was busy.

This was more routine for Ms. Caramel. Clients at the club, even her boyfriends, usually ending up being the subs in her relationships. Scott was now just another boy, on his knees licking her pussy. She felt the familiar tingle of her orgasm as it washed over her. She bucked and grinded, cumming onto Scott's face as he licked and fingered her to climax.

"Oh yes, good boy. Good boy, I'm cumming, YESSS, I'm cumming!"

The bouncers outside glanced at one another. Sherry (Mistress Caramel's real name) didn't usually scream that loud. But, they didn't want to risk barging in on one of her performances. One bouncer had run in on her and one of the Montreal Canadians and the hockey brawler beat the shit out of him. To add insult to injury, the club owner fired him.

Inside the booth, Sherry had finished cumming over Scott's face and lay back on the bench. Her legs spread wide open, arms over her head, and eyes closed; she was the image of temptation. Seizing his opportunity, Scott rose from his knees. Her pussy wet and legs spread open, he easily slid his hard cock into Sherry.

"Oh god," she murmured, still in a blissful reverie.

Scott quickly put his fingers in her mouth to silence her moans. She licked her juices off his fingers like they were his cock just minutes before. He thrust himself deep into her pussy. She was so wet, he easily slid in and out. The soft flesh of her thighs felt so good against his toned stomach. His white cock pumped in and out of her dark pussy. The contrast between man and woman, white and black, felt so good, so right.

"Oh Mistress, yes. Yes!!" Scott forced himself to slow down. He felt a strong desire to pound into this gorgeous, voluptuous woman, but he wanted to hear her cum. He began slowly withdrawing his cock from her, thrusting lightly into her once, only an inch or so, then in deeply nine times. Lightly twice, then deeply eight times. Trying to keep his wits about him with the trick, counting and thrusting to ten light, shallow strokes.

Writhing beneath him, Sherry was amazed at how well Scott was fucking her. Teasing her pussy so well. By the time Scott got to ten, she craved the deep strokes from his cock more than the air she needed to breath.

"FUCK ME, YES!" She hollered at him, her hands firmly grasping his ass pulling him to her. Her nails were dug deep into his muscular ass as he pounded into her with full, long, deep strokes.

"Oh yeah, you like my big, white cock in your slutty wet pussy don't you? Don't you bitch!"

"Yes, yes, fuck me. Keep fucking me!" Sherry urged him on.

"Yeah, you slutty tease. Teasing me with those brown eyes, those big black breasts, and that sweet ass!" Scott grunted out, verbally releasing his pent up frustrations.

"You like my body baby? You like these big titties? You loved licking my black pussy didn't' you, horny white boy. Fuck that pussy now, fuck me!"

As he could feel his orgasm building, Scott knew he would have to cum soon. He needed a second to slow things down and he was dying to take Sherry from behind. That amazing round ass that had hypnotized him earlier. He'd fantasized about a woman like Sherry since seeing his first rap video and he knew he may never have a chance like this again.

"I need to have you from behind!" He said to her in a tone as seriously as he could muster. He pulled his cock from her pussy, feeling the cold air of the club and missing the warmth of her sex immediately.