Lena Ch. 01

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Lena helps boyfriend settle a gambling debt.
4.7k words
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Part 1 of the 11 part series

Updated 11/02/2022
Created 01/11/2005
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Buzzboy
Buzzboy
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Chapter One - The Dutiful Girlfriend

Lena watches the city streets in the late night from the passenger side window of her boyfriend's car. Having quick glances of the different groups of friends, street entertainers, bikers, cops as she goes further in the city. Though Lena would find the drive mildly enjoyable, she finds her boyfriend's choice of destinations less than appealing. She thinks back how she angered Chad by insisting on going to a movie with her friends, how his description of Lena being a selfish and ungrateful girlfriend made her feel guilty and ashamed enough to apologize for not being the girlfriend Chad deserved.

Chad drives in a dark back alley and stops at the back parking lot of a building.

"Honey, why don't we skip this one tonight? Let's go somewhere else." Lena pleads.

"What?" Chad says with a sudden scowl appearing. "You fucking stupid? You don't think I can win?"

"No, I'm not saying that?" Lena answers, trying to calm down Chad before the conversion grows more unpleasant. "This is different than your usual poker games." Instinctively Lena attempts to slowly move from the infuriated Chad, but Chad quickly grabs her arm and pulls her to him.

"You saying I'm going to lose!" Chad yells at Lena's face. "I can't win! Is that what you're telling me!" Lena sees the hate in Chad's eyes.

"I'm sorry." Lena says. "I should know that you know what you're doing. I shouldn't have said anything." Lena's apology begins calm Chad. Lena sees the hate disappear and slowly became the handsome man she fell in love with.

"It's okay, babe." Says Chad, smiling. "Just watch what you say to me, especially around people, okay?"

"Okay." Lena responds.

"And I'm not going to lose, baby. You're my good luck charm. That's why I need you here with me." Lena feels the comfort she needed by Chad's words. "Now, are you sorry?"

"Yes." Chad releases his grip on Lena's arm. Lena rubs her arm as she sees Chad undo his belt.

"Come on. I want a blowjob before we go in." Chad takes his erect cock out. Lena is hesitant. "Lena." Chad mildly asserts.

"Fine." Lena submits, thinking it well be easier to give him the oral pleasure he needs than not to in his volatile state.

"Get naked." Chad orders. "I want you to blow me naked." Without saying a word, Lena obediently removed her jacket, then her shirt, then unhooks her bra exposing her breasts, she slips out of her skirt and then her panties. Chad slowly strokes his hard cock as he watches Lena strip. Wearing only her pumps, Lena sits back for Chad to see her nude body. Lena then leans forward and slowly puts Chad's stiff member in her mouth. Lena hears Chad's moans as she motions her head up and down caressing his hard cock.

"Go faster." Chad orders. Lena does so, causing Chad's moans to be more intense. Lena focuses her complete attention on sucking Chad's cock, stopping to gently stroke the member and roll her tongue on the head while she catches her breath. She begins to taste Chad's semen on her tongue. Lena sucks her boyfriend's cock as fast and hard as she can.

"That's it, you slut!" Chad blurts. "Keep going! I'm gonna blow in your mouth!" Chad puts a firm hand on the back of Lena's head. Lena strokes the base of Chad's cock as she continues to suck and lick.

"Yeah! I'm coming! I'm coming now!" Simultaneously Lena feels Chad's grip on her head tighten, as she tastes the rush of jizz shooting in her mouth.

"Swallow all of it, slut!" Chad demands. "All of it!"

Lena begins slow down but continues sucking the spent penis for a few minutes until Chad pulls her head off his lap. Chad tucks his penis back in his pants as Lena sits back on her seat.

"Was it good?" inquires Lena.

"Yeah, real good." Chad answers, fastening his belt. "I'll want another one later tonight after the game."

Lena smiles at Chad's approval of her oral sex abilities and wanting more from her. She remembers how she almost lost Chad after her first try at oral sex with him. Chad understood that Lena wasn't ready for actual sexual intercourse this soon in their relationship, but Chad made Lena understand as his girlfriend, she has to gratify the sexual urges she unintentionally gives him. The first time was in Lena's bedroom after her 18th birthday. She was nervous and hesitant. During the blowjob, Lena tasted Chad's semen for the first time. Chad didn't seem satisfied with her efforts, so he walked out without a word. Lena recalled the emotional devastation she felt, wondering if Chad would ever allow her to please him.

She then recalled the relief she felt the next day at their private school. Lena pleads to Chad earned her another chance to show her love by sucking his cock, when Chad lead Lena to boys' locker room. Being the only two there, privacy was insured for them. Chad commanded the eager to please Lena to take off her clothes. Lena reluctantly obeyed. She remembers how nervous she was standing in front of her boyfriend completely naked. Soon she was on her knees sucking Chad's cock.

Since then, for months, Lena's blowjobs to Chad were her way to love him. Everyday at their boarding school, Chad and Lena would sneak in the boys' locker room when it's empty, Lena would be naked and orally please Chad. Each time, she would do better, give more effort, use her hands more, use more saliva.

"What are you doing?" Chad assertively asks, putting Lena back to her present situation.

"What?" Lena replies.

"Put your fucking clothes on!" Chad demands. "You want to go in there naked, you slut? Give all the guys blowjobs?

"Sorry." Lena gathers for her clothes. "I forgot – and –"

"Just get dressed. And fix your makeup."

As Lena put her clothes on, she reminds herself that Chad loves her dearly, as long as she can perform her girlfriend duties.

The poker game took place in the only occupied table a small restaurant. Chad sits at this table with five other men. Lena sits at the bar, drinking soda to wash away the taste of semen in her mouth. Looking at Chad and the other player, she notices how Chad is certainly the youngest at the table.

Lena watches Chad with concern of the outcome. Her friends warned her that Chad is a compulsive gambler and on several occasions, his father had to bail him out of the predicaments he gets himself in. She faces away from the poker game, wishing not to distract Chad. For the past two hours, Lena would occasionally look at the poker game to check on Chad's progress and each time, her boyfriend would go from appearing confident and calm, to worried, to utter desperate.

Finally, the players would leave one-by-one, only Chad and a stern looking man in his late 30's sits at the table. Lena watches Chad desperately plea to the older man, she knows he lost big. She watches this for almost twenty minutes until Chad get up and hurries to her.

"How much?" Lena asks.

"I owe – I owe that guy –" Chad tries to control his frantic mood. "Four thousand dollars."

"Oh, my god." Lena's mouth drops. "Your dad is going to freak when he hears this."

"No!" Chad growls through his teeth. "I'm not going tell him." Chad pauses to wipe the sweat off his brow. "Dad said if I gamble again, he'll send me to a military school. A really strict one."

"That guy you were talking to, can't you reason with him?" Lena questions.

"I can't. Eddie said if I don't pay him now, he'll brake every bone in my body."

"How could you do this?"

"Lena, honey, listen. You have to help me get out of this." Chad pleads.

"How? I don't have that kind of money. If I ask my parents, it'll take a while cause –"

"No. Not like that." Chad pauses to catch his breath. "Eddie won't hurt me...if you go with him."

"Go with him where?" Lena replies, dreading the answer to come.

"To his place." Chad responds. Lena feels a knot forming in her stomach.

"No, you're not suggesting I sleep with him?"

"I don't have any other options."

"But I want you to be my first?"

"So do I, but this guy well kick my ass if you didn't go fuck him."

"Call your dad. Get him to –"

"NO!" Chad bursts, and then composes himself again. "Dad well send me away. Away from you. Lena, baby, you gotta do this for me." Lena tries to reason with her frantic boyfriend, but Chad speaks before she can. "You love me, right? You'll do this for me?"

"Okay, I'll do it." Lena finally gives in. "But I want you to promise me that you'll stop gambling."

"You do this for me and I well." Chad said.

Lena takes a deep breath and walks to the man at the table. Eddie, a tall, burly man, looks at Lena with anticipation. Lena notices Eddie's expression, forcing herself to continue her pace to him.

"Hi, I'm Lena." Lena states.

"I'm Eddie." Eddie replies, looking over Lena. "Ready to go?"

Lena sits in the passenger seat of Eddie's porch. On the half-hour drive to Eddie's house, conversation between Lena and Eddie became minimal. Eddie did tell her that he owned the restaurant they left and three others. Lena felt too nervous for small talk, she reasons with herself that the sex with Eddie well probably last an hour then she can go home and Chad well be so grateful to her for her sacrifice. Allowing herself to lose her virginity to a man she just meet instead of her true love.

"Ah, Eddie?" Lena softly speaks. "Chad probably didn't tell you, but I'm a virgin."

"Yeah, he told us." Eddie replies.

"Us? You mean you, right?"

"No, Chad said you're a virgin at the game." Eddie briefly looks at his passenger with a grin. "He also said you give good head."

Lena quickly covers her face to hide her shame.

"So it's true that you blow him everyday at your fancy school?" Eddie questions.

"Yes." Lena answers, moving her hands from her face.

"Naked and in front of his friends?"

"What?" Lena reacts. "No, not is front of his friends. Did he say that?"

"Yeah, but hey, maybe he was lying. Guys do that."

Lena feels her stomach sink at the thought of Chad inviting his friends to spy on her sucking her boyfriend's cock naked in the boys' locker room. Moments with Chad she thought were intimate and private. And then telling his poker pals all about it.How could he do that? Lena thinks.

Finally making it to Eddie's home, a modern two-story house in a rural area. Lena mentally prepares herself for her task. Eddie takes her coat and guides her to the living room, standing her in front of a black leather couch. Instinctively, Lena stays her spot as Eddie sits on the couch.

"Take off your clothes, now." Eddie bluntly orders. Giving no resistance, Lena begins to strip. Eddie watches her slips her bare feet out of her pumps, then she unfastens her skirt, letting it drop down to the floor, revealing her panties and well-toned legs, she unbuttons her blouse and drops it on the floor showing her equally well-toned arms, she reaches behind her and unhook her bra, exposing her beautiful breasts.

"Very nice." Eddie comments. "With tits like those, no wonder Chad needs a blowjob everyday."

Lena continues to strip, as she is about to gently pull off her panties.

"Turn around." Eddie commands. Obeying Eddie, Lena turns her back to him, figuring he wants to look at her ass. Lena pulls her panties down and bends forward slide them all the way down, giving Eddie a magnificent view of her firm ass.

Putting aside her modesty, Lena tosses her panties on the pile of her clothes, stands straight with her back to Eddie for a few seconds.

"Do you like what you see, so far?" Lena asks, trying to appear calm and willing.

"Come here, sweet cheeks." Eddie commands. Lena walks to the couch, forcing herself to smile. "Sit on my lap." Lena does so, placing her bare bum across Eddie's legs and sits up as straight as she can. She feels his erection through his trousers on her ass.

"Would you like me to suck your cock?" asks Lena, hoping to get her task over and done with.

"We have all night, babe, so relax." Says Eddie. "I'd like to know more about you."

Considering that Eddie has been reasonably nice to Lena, she tries to relax and open up to him.

"Okay, what do you want to know?"

"How long have been dating Chad?"

"Four months, two weeks and three days."

"You're both at the same school?"

"Yeah. When I first saw Chad at the beginning of the school year, I just know that he's the man for me."

Lena feels Eddie's hand on her lower stomach and begins making small circular motions.

"Really? At first sight?" Eddie asks.

"Oh, yeah. He's incredibly good-looking, he has a cool car, his dad owns a big shipping company and he lives in a huge mansion."

"And you two haven't had sex? Just blowjobs?"

"Yes."

Eddie's hand slides down to Lena shaved pussy, but her joining thighs block the way.

"Spread your legs more." Eddie instructs.

"No, wait. I..." Lena defensively reacts.

"Lena." Eddie calmly asserts. "We're really beginning to get along here. Now if you want leave and forget all this, then that's fine. But if you're going stay, you do what I tell you."

Lena reminds herself about Chad's gambling debt and why she is with Eddie.

"I'm sorry." Lena by habit apologizes as she parts her legs. Eddie's hand moves to her exposed pussy and slowly strokes her clit, causing Lena to softly moan. She then feels a finger slowly forced into her moist canal, giving Lena sensations of pleasure and pain.

"So you are a virgin." Says Eddie.

"Yes." Lena gasps, feeling the finger move inside her.

"Where else have you blown Chad?" asks Eddie, returning to his questioning.

"Other than the locker room: I blew him in my bedroom, his bedroom, his parents' bedroom. Then that got old for him, he made me blow him in alleys, public washrooms, and one time at the theater." As Eddie continues to interfere with Lena's tight virgin pussy, she could not give any resistance to him.

"What would your parents say about this?"

"They don't know. They wouldn't care anyway. Dad's always away on business with his slut assistant and I think Mom's at a new-age mountain retreat fucking all the towel boys there."

"So it's just you at home?"

"And the maid, whose been drinking since my dad dumped her for his assistant."

Eddie pulls his intruding finger from her pussy. Lena starts to catch her breath, but her pause is cut short as Eddie moves his pussy soaked finger to her mouth.

"Suck on it." Eddie commands again.

The sooner I do this, the sooner it well be over. Lena thinks. She closes her eyes and opens her mouth. She closes her lips over Eddie's finger and begins to suck with great effort. Lena's mouth wraps around the finger, sucking all the pussy juice. Lena feels Eddie's erection pressing on her ass grows. Finally, Eddie pulls hand away Lena's skilled mouth.

"That was nice." Says Eddie. "Now I want to fuck you." Eddie hooks his arms under Lena and holds her as he stands from the couch and walks to his bedroom, carrying Lena in his arms.

Lena finds it romantic being carried to the bedroom by Eddie. She often fantasizes it would be Chad to carry her off to an elegant bedroom, maybe a room at a posh hotel. Lena is hopeful that after this night with Eddie, she and Chad well be closer together, especially since he promised to stop gambling.

In the bedroom, Eddie gently places Lena on a satin sheet bed. Eddie begins taking off his clothes. Lena sees the impressively muscular build on Eddie, and then he removes his shorts and to her surprise sees Eddie's hard cock, bigger than Chad's by length and girth. Lena moves herself to seat on the edge of the bed, facing Eddie. Lena gently takes hold of Eddie's member and slowly strokes it. She closes her eyes, takes Eddie's hard cock in her mouth and begins the sucking motions.

"Damn, girl." Eddie moans. "You really are good."

Eddie reaches to open a drawer the nightstand next to the bed. Lena opens her eyes, seeing Eddie take a small blue pill and shallows it. Lena closes her eyes again and focused on pleasing Eddie's member. Eddie gently holds Lena's head and slowly pulls her away.

"Get under the sheets."

Lena pulls the bed sheets as she slides under them and lies on her back. Eddie follows immediately, moving beside her. Lena feels Eddie's cock brush against her leg. She braces herself for her deflowering. Eddie positions himself and his hands and knees over Lena, he lowers his head to press his mouth against Lena's mouth. Lena feels Eddie's tongue force its way in. Unable to contain his disgust to maintain her ruse, she pulls her mouth away.

"Hey, relax." Eddie recommended. "You'll enjoy it more."

"I just want this over with and go home." Lena states, still looking away from the man above her.

"I said we got all night. All night."

"What was that blue pill you took?"

"It's your first time. You don't expect me to blow my load in you and then call it a night within twenty minutes?"

"Christ, you're using boner pills?"

"Like I said, babe. All night."

Eddie grabs Lena by her hips and pulls her to him. Lena suddenly feels Eddie's cock push itself in her vagina, then pain as her hymen brakes, ending her virginity.

"Jesus, you're so tight!" Eddie exclaims.

Lena closes her eyes and grabs the headboard above her as she moans at Eddie's pelvic thrusts. The pain begins to lessen after her cherry popped, but not by much.

"Oh, fuck!" Eddie cries out, more excited. "Your pussy's so fucking tight!"

Lena's mind goes inward to the pain coming from her sex and focuses on a source of pleasure growing inside. The thrusts get harder and harder as her moans grow more intense.

"HARDER!" Lena blurts. "FUCK ME HARDER!"

Lena's demand fuels Eddie's lust, doubling his efforts.

"Yeah, you like this, don't you slut!" Eddie boosts.

"YES! YES!" Lena replies with lust. "KEEP FUCKING ME! PLEASE! PLEASE! DON'T STOP! DON'T STOP!"

Lena is shocked by the words she just said in the thralls of intercourse, as if her body has betrayed her and surrendered to the fleshy intruder violating her wet, once-virginal channel. In her mind, she wonders how could she have gone from a properly raised, loyal and faithful girlfriend to a lowly common gutter slut...and why does it feel so, so good.

"FASTER! PLEASE GO FASTER!" Lena begs, opening her eyes to seeing the eyes of the man fucking her. Acting on her newfound carnal instincts, she lets go of the headboard and vulgarly grabs her tits, provoking more lustful arousal from her deflowerer. Eddie suddenly grabs Lena's legs by the back of her knees and pushes them to her. Lena's pleasure deepens as Eddie's penis does the same. Lena closes her eyes again, savoring the sensations.

"YES! GOD, YES!" Lena yells. "I'M GONNA COME! FUCK ME, EDDIE! FUCK ME!"

"Tell me you love this!" Eddie orders. "Tell me you this or I'll stop right now!"

"YES!" Lena responds without thinking. "I LOVE THIS!"

"You're my slut tonight! Say it! Say it!

"I'M YOUR SLUT! I'M YOUR SLUT!"

Lena keeps repeating her last statement until she feels a rush of warm fluid from the penetrating cock in her sex. She waits for a few seconds until finally the fire growing between her thighs consumes her. The burning pleasure of her orgasm became more than Lena anticipated, putting her in a state of euphoria.

Eddie falls backward and begins to catch his breath, laying flat on the bed with his cock still standing erect. Lena opens her eyes and to her amusement and excitement she see Eddie's member hard and stiff, as it was when it was mercilessly fucking her. Acting on a combination of lust, the throbbing sensation from her pussy and primal animal instinct, Lena crawls to Eddie. She starts a series of wet, passionate kiss his stomach, up to his chest, to his neck and then his eager mouth. Lena then gently holds Eddie's cock and lowers her pussy into it. She feels the pleasures of the penetration once again and bounces herself up and down.

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