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Lindsay Steph and 21 Gangsters

Lindsay Steph and 21 Gangsters

by Driftwood55
19 min read
4.13 (4500 views)
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Lindsay, Steph and 21 Gangsters - Cheerleaders Lindsay and Steph take a shine to 21 Gangsters in a New Orleans Manor

Welcome readers. This is part six in the Cheerleader Lindsay series.

Lindsay is a junior transfer student at Baylor Tech and a member of the cheerleading squad. Her wild sexual adventures evolve from a bet between rival football teams. Baylor Tech loses to Virginia University, leading to Lindsay meeting up with five aggressive jocks at a warehouse.

The sexual rollercoaster continues the next day when she is pulled over by two undercover detectives working in the rough part of town. Three younger cops join them at an abandoned toy car factory to dominate Lindsay.

Returning to campus, Lindsay gets into a fight with her boyfriend Jake. Joe and Sean witness the fight. They interfere, Jake leaves, and her rescuers take Lindsay to the Baylor Astronomy Observatory for wild times.

Chapter 4 details Lindsay being summoned to the Dean of Students, Mr. Phillips' office. Police Chief Conrad and football coach Aberdeen join them. The three older men, having learned of the wager with Virginia University, grill Lindsay and threaten her with expulsion. In desperation, Lindsay utters "Eagles over Broadway", a phrase the detectives told her to say if she got into trouble. Police Chief Conrad is duped. Thinking Lindsay might be an undercover agent, they strike a deal. Lindsay will scout the football team's upcoming opponents. She will be unhindered as she looks for drug connections and playbooks. Her first trip is to Louisiana.

The series continues with Lindsay's friend, Stephanie, coming out for a visit to New Orleans. While Steph goes out to research a famous historical figure, Lindsay meets up with Derek and a few of his football-playing friends. Wild sex ensues and her new playmates get Lindsay to reveal her darkest fantasies. An evening of debauchery is now set into motion.

Lindsay, Steph and 21 Gangsters - Cheerleaders Lindsay and Steph take a shine to 21 Gangsters in a New Orleans Manor

"I hope this is the right place," Stephanie said to the Uber driver, Jacques, as he pulled the dark Jaguar I-Pace up to The Blue Hornet Pub.

"What time are you supposed to be meeting your friend?" Jacques asked gazing back at the spunky blonde in the back seat.

Stephanie noticed Jacques eyeing her in the mirror. She wondered if he was trying to flirt with her. Putting her lipstick down, Steph tapped his shoulder and sighed, "Not 'til 10 p.m. Looks kind of quiet."

"It's only 8:30," Jacques observed. "The Horny Den will be jumping later."

"Well, I sure hope so," Steph said, bubbling over with excited anticipation. "You probably could guess I am from out of town."

"I was wondering," Jacques responded with a grin. He was used to getting hit on while driving. Usually, trying to keep a focus on his earnings he would get the occasional phone number. Tonight was different. Jacques mostly drove on the weekends, but this was a week night. It was much slower than he anticipated. "I'll give you a little tour of town if you like. That way you'll have a little more time to do your makeup."

"Really? Sure if you have time," Stephanie responded pleasantly surprised. "I don't want to mess up your schedule."

Jacques angled his Jaguar over a hill with nice views of the city. "You won't find this vantage point in the guidebooks."

Stephanie was relieved Jacques had pulled the car into a parking spot. "Thanks for stopping. I can't really do my eyeliner when we are moving."

Bewildered that she wasn't impressed with the stunning perspective Jacques tried to shift the conversation. "If you have a competition going with your friend you'll win."

"Competition?" Steph asked, pondering what Jacques meant as she continued to devour the sculpted features of her handsome driver. "What do you mean?"

"Eye liner or not you got my eyes worn slap out. Gussied up in that full length black dress you are going to cause a stir of hankerings for smashing," Jacques said as he stared at how well Stephanie's bodycon dress displayed her big tits.

"So the Horny Den, eh?" Steph asked, blushing over Jacques' attention. "I hope so. I'm so fucking horny. Whoops." She giggled nervously and quickly added, "You are kind of right about competition. My friend is one hot chick. She's not short like me and she's already hooked up with some guys here. I am just hoping they have a few friends that I can..." Steph paused. "What did you call it? Smash, right."

"That's right. You keep talking like that and you'll cause a riot in The Blue Hornet," Jacques answered calmly as he was doing his best to turn on the charm with his body language.

"You glide well. You are so smooth." Stephanie declared in appreciation of his efforts. "I also have my new secret weapon, which I haven't even tested out yet." Stephanie pouted her lips and then opened her mouth revealing her new tongue ring.

Jacques' libido did a back flip as his state of arousal broke orbit. "Hot damn. Holy, finer than a frog's hair split four ways."

Their noses were almost touching having moved closer. "I don't know what it means, but I think I got you excited."

Steph put her mouth on Jacques' lips and they exchanged passionate kisses. Jacques helped Steph pull herself into the passenger seat. After exchanging saliva for a few more minutes Stephanie had her hand on Jacques cock as it was now getting fully erect in his pants.

"Wanna help me break it in?" Steph asked coyly as she clicked the stud of the tongue ring against her teeth.

Jacques smiled back at Steph while he pulled the car seat back. "Go for it."

Stephanie unzipped his fly freeing Jacques' sizable snake. He was a solid eight inches and very thick. She started licking her tongue up and down his shaft. Jacques placed his large hands on the back of Steph's head. "Put it in your mouth."

Gagging sounds got louder and louder as Steph tried her best to deep throat Jacques while getting used to the new hardware in her mouth. "You like it? I mean the tongue ring."

"Ain't you nothing," Jacques answered.

Disappointed, Steph stared back at him and said, "I guess I better use my hand." Steph started to quickly stroke Jacques' cock.

"Whoa, damn, you got some hot little hands," Jacques stammered to explain. "I think you misunderstood. Ain't you nothing means you are bussin. It means you are awesome."

"Oh," Stephanie replied, now beaming with reassurance after fearing that maybe her tongue ring didn't feel so great. They locked lips and kissed passionately.

Jacques' cock ached as his balls had become full of lots of sperm. Guiding Steph's mouth and her magic tongue ring back on his boner he held her head steady. "Right there. Use the ring on the head of my cock. Nice and slow."

"Like that?" Steph struggled to ask.

"Oh, yes. Just like that. Now guide the post around the underside. Oh, fuck yeah," Jacques moaned.

Stephanie was getting aroused as his groaning got louder and he started to breathe faster. "There you go. Give me your cum."

Jacques' eyes lit up. He was responding to her dirty talk. "You are going to get it now, you little slut."

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"Shoot your snake down my throat. Make me a nasty slut tonight," Stephanie urged.

The idea of further adventures with this hot vixen was too much for Jacques. "Oh fuck. I'm fucking cumming. Take my cum. That was so fucking hot," he belted out as Steph felt his cock firing jolts of cum down her throat.

She pulled his cock out of her mouth while he was still cumming. His semen had a nice flavor, but she wanted to feel the warmth of his cum on her cheeks. "Cum on my face," she begged.

"Oh yeah," Jacques yelped as he stroked his balls dry shooting a nice long rope of cum across a cheek and over one of Steph's eyelids. She licked him clean and then freshened up.

They shared a laugh as Steph told him she did notice the grand view of the city. She didn't say anything because she was more focused on him. "Let's go to the bar," Steph suggested.

"I'll take the night off and I'll go on one condition," Jacques said, looking very devilish.

"And what would that be?" Steph asked, ramping up her sexy voice.

"Bussin' tongue ring, hot little hands, I'm dying to feel your pussy grabbing my cock," Jacques answered so confidently, Steph seriously considered taking him straight back to her hotel room.

"So you want to fuck me?" Steph asked, teasing Jacques.

"I want to see how nasty I can make you," Jacques answered. He was nodding his head. "Oh yes, indeed, you better believe I am going to take up the challenge and push you."

"Sure you think you can do that?" Steph said, toying with Jacques. "With a rare visit like this, I would hate to be disappointed."

"Oh, your friend picked the perfect location," Jacques whistled as devious plans started to form in his head. "Just listen to me and don't be afraid."

"Don't be afraid of what?" Steph asked. She was getting equally aroused and intrigued. She wanted to hear more but hoped Jacques wasn't going to tell her everything.

"Of how nasty you're going to get," Jacques answered. "Don't turn into a tease on because your friend is there and you get embarrassed."

"Oh, it's not like that," Steph sighed. "She knows I'm a little wild, but she's wilder and doesn't talk about it. If anything, I'd like to really surprise her for once."

"Really?" Jacques asked, taking a deep breath. Steph nodded. "Obey, do as I direct," he commanded.

"Okay," Steph responded while caressing Jacques' cock, which was back in his zipped-up pants.

They made their way to The Blue Hornet. Jacques turned to Steph as they got out of the car. "Safe word?" he asked.

"Don't build up my expectations too much," Steph giggled with sass.

Jacques' open palm slapped loudly against Steph's bodycon dress.

"Wow," Steph moaned. She smiled. Jacques was adapting well to being more dominant. She was turned on by the hopeful thought she had underestimated him.

Inside The Blue Hornet they found a table in the back room. The place was starting to fill up, but Lindsay wasn't there yet. Jacques waved to a few people and a few guys stopped by to visit and meet Steph.

Jacques did a good job of holding court. He kept the attention on Steph, letting her bubbly personality dazzle the sexual energy that was permeating the room. If anyone ogled her tits for too long or pushed the conversation beyond subtlety, Jacques was quick to give them a hidden cue to leave.

After meeting five or six of his friends, Jacques grabbed her by the wrists and they kissed. They had the table to themselves. He adjusted her bodycon to expose more of her cleavage. "That's better," he declared. "I can tell what kind of guys turn you on."

"Can you?" Steph asked whimsically. "Am I that obvious? I wasn't fawning over anybody."

"You are good. You were not too obvious," Jacques answered.

"I didn't make you jealous, did I?" Steph asked, trying to see where Jacques' mind was going.

"No. Dominating you to make you feel pleasure is what gets me going," Jacques explained. "So, you did find a few of the guys attractive?"

Steph smiled and blushed a little. She thought of the third guy who came to the table. Draymon, a large muscular African-American bad boy type. He was pretty rough around the edges, but very good-looking. "You got one or two friends that are pretty hot."

"Hmmm," Jacques said as he rubbed his chin. "Good."

As Jacques tugged her top a little more to the side, revealing even more of Steph's nice rack, she helped him as she jumped up.

"Hey Lindsay, over here," Steph yelled to Lindsay, who walked in with Derek, Steve, Leo, and Walter.

Jacques was acquainted with Derek and Walter. After introductions and a round of drinks, Steph and Lindsay made a trip to the restroom.

"So, you just met Lindsay's friend?" Leo asked Jacques.

"Fortunate lads we are," Jacques answered, grinning. "Look, I'm picking up the vibe you all are on a mission and I am right there with you. I've got a mission too."

Walter clapped one hand on the freshly snapped thumb of his other hand. "You're picking up the vibe. Tuned up and ready to wreck."

"Logistics? Where we are going?" Leo asked. "I know you all, on the football team, know the drill on getting the right guests."

"For sure," Derek and Steve responded. "Extras: timed, regulated, and subtle but effective. You know we have the Magnolia Manor all set up."

"No shit. So that place really exits? Well, when we get there you'll have to give me space to chill the short sassy blonde for a bit," Jacques cautioned. "Once I signal, bring in the BBCs and the bad dudes."

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"You are good, bro. Derek and I were born into The Tradition of The Minders," Walter conveyed in an oddly harmonic tone. Walter grabbed Jacques' wrist and mouthed the address of the Magnolia Manor. "Don't write it down. Turn your cell phones off before you leave the bar."

Jacques, having grown up in New Orleans, knew The Tradition of The Minders was a very powerful and secretive association. He made the sign of the cross to indicate he understood.

"What are you boys up to?" Lindsay laughed.

"I thought I heard them say BBC," Steph giggled.

"You probably did. Boys talking about cock. Ha ha, they are gay, I told you," Lindsay said brashly. "So, are you dreaming of your favorite obsession again?"

Steph blushed and put her hands over her face. "So what?" she asked as Jacques grabbed her hand and stuck one of her fingers on his tongue.

"Don't be shy about your talents. Show it off," Jacques urged.

Steph understood his message. "Maybe I was hoping to put this to good use," she confessed in a sexy voice while opening her mouth. Her tongue ring sparkled as it caught the light of The Blue Hornet bar.

Her boldness and the instant vision of feeling her tongue on their cocks sent an erotic jolt through the group. Without saying anything further, everyone understood a thrilling dynamic. Steph and her firecracker personality had submitted to do Jacques' bidding for the night.

The group then turned its attention toward Lindsay. "You questioned our sexuality? Is that because we are comfortable around each other inside you?" Derek asked. It was his way of teasing Lindsay. He was letting her know her next session would be more intense to help her remember.

Lindsay instantly felt aroused now that she had inadvertently given them a challenge to be more dominant and aggressive. She winked at them and conveyed if she was to be punished, Steph, by association would, also be in trouble.

When Steph wasn't looking Lindsay made subtle gestures at her while looking to make sure, the guys were paying attention. It was as if Lindsay had a bullhorn and was saying, "Make sure the blonde hottie gets it good."

To Lindsay's delight, Derek let her know she would be witnessing the assertive corruption of her fellow cheerleader. "Don't worry, I wouldn't want you to miss what happens to her," Derek whispered in Lindsay's ear while tugging on her ass.

Lindsay smiled back at Derek. She softly asked, "Hey, you got a vigorous plan, then?"

"As audacious and as saucy as she is, we be fixin' to make her get wild as all get-out," Derek replied. "You'll see. I expect it will make you as wild as a June bug on a string."

"You sure have some funny expressions down here," Lindsay said. She liked how relaxed Derek made her feel, even when he exerted his devious side.

"Let's move this little party, shall we?" Leo asked as he toasted the group and finished his beer. "Jacques, why don't you drive the ladies over."

Derek handed Jacques a couple of pairs of blindfolds as they left The Blue Hornet.

"Lindsay and Steph, before we take off, I need to put these on you," Jacques insisted. "Turn your cellphones off and give them to me."

"Pretty silly," Lindsay remarked. "Do you even know where we are going?"

"Come on, lighten up, it will be fun," Steph offered in favor of wearing the blindfolds. "Your other senses will be heightened and you can let your imagination run wild."

"Okay, I'll pretend we're going to a top secret location," Lindsay relented. She closed her eyes while Steph placed the blindfold over her hair. Lindsay giggled, "Your pleasure zone isn't really a sense, but get ready for some increased friction-induced sensitivity."

Jacques and Stephanie burst into laughter. Once he regained his composure, Jacques placed the other blindfold on Steph. As they drove to a secluded Victorian on the edge of town, Jacques laid it on thick that they were two captured spies.

Their destination was a four-story house in an industrial part of town. It was one of the few houses that remained from a bygone era. Built in 1870, it was one of the Victorians constructed all over the city before electricity was available. When the light bulb replaced the oil lamp ten years later, the city changed its development plans.

Nestled on the grounds of a large manufacturing warehouse, the house was not easy to find and couldn't be seen from the road. These days, the larger site was used for overflow storage as the main operations were now out in a rural area.

The use of the house had been passed down from generation to generation. Walter and Derek were born into the group that regarded the house as a secret playground.

Jacques led Steph and Lindsay from his Jaguar I-Pace up the creaky steps of the house.

"Ouuuweee, creepy and mysterious," Lindsay observed.

"Here are the spies," Jacques announced as they heard a large door opening.

Jacques held Steph firmly by the shoulder as Lindsay was led into a room nearby. Steph listened to Lindsay's footsteps fade and then heard a door close. Steph moved to remove her blindfold, but Jacques quickly grabbed her arms. "Not so fast," he snickered.

Jacques bound Steph's wrists together with rope and led her up several flights of stairs.

As Jacques ledi her down a hall and into a room, Steph heard Jacques latch the door shut.

"Alright, spy with the hot hands and magic mouth." Jacques whispered as he ran his hands up and down Steph's bodycon dress.

"You gonna untie me," Steph moaned as Jacques was forcefully squeezing her breasts.

"As long as the first thing you do with your hands is to help me get you out of this dress," Jacques insisted as he unbound Steph. He removed her blindfold once she had stripped down to her lingerie.

"Wow, sexy red decor," Steph declared, finding herself in a very red room. The walls and ceiling were covered in red wallpaper with an elaborate design. It was a bedroom with a scarlet carpet and a large bed with a crimson velvet bedspread. Jacques and Steph started kissing with runaway lust and passion.

Jacques had been thinking about getting his cock inside Steph from the moment he helped her climb into the front seat of his car. Biting, slapping, and rolling around, they made the velvet bedspread their erotic playground.

"Oh fuck," Steph cried out as she felt Jacques' engorged cock sank into her pussy. "Oh fuck, you are big. Wow, you feel so fucking good." Steph had anticipated the warm and stuffed sensation. After using her new tongue ring on Jacques' snake, she had eagerly waited to feel him pound her pleasure zone.

Jacques quickly ramped up his pace and got Steph into a doggy style position as he thundered away relentlessly. He pushed himself deep inside her. While grinding against her hips, he turned her head around to kiss her.

"Oh fuck. Oh shit. Shit. I'm fucking cummmmming," Steph screeched as a powerful orgasm overpowered her like a rogue wave hitting a cargo ship on the open seas. "I'm cumming all over your cock. Oh, you are fucking me so good."

"Oh yeah. Fuck yeah," Jacques yelled as his dick erupted inside Steph's pussy. The blast of his warm cum sent a shiver through Steph's body. Jacques kept kissing and caressing Steph's smooth skin.

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