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Juan had a good first week.
Fresh out of college – not even graduated yet, technically – he’d landed a job at the second largest consulting firm in his home city. It paid $45,000 a year, with benefits. Juan had never made more than $12 an hour.
The work was great. His manager threw a few clients his way on day one, and Juan seemed to really click with them. He even had a few leads on fresh clients of his own.
And the girls! Juan couldn’t believe it – this company was better than business school. Nothing but trim, pretty women in pencil skirts and high heels.
Juan mostly kept to himself, but he’d made a promise to be more outgoing at the new job. To him, college had been a series of missed opportunities. Those business school girls flirted with him often – a few had even drunkenly propositioned him outright. But Juan never had the courage to pull the trigger.
As a 22-year-old virgin, Juan had perfected the art of masturbation. He’d done it everywhere: in the car, on the phone, in public bathrooms.
He wasn’t a freak or anything. But when you’ve spent years masturbating, some variety is required. Juan, a right-handed man, had become ambidextrous by the age of 16. He’d used more lotions than he could count. He even tried a Fleshlight once, though it left him so disgusted he had to throw it in a dumpster outside his dorm.
To encourage himself to be more outgoing, Juan vowed to give up masturbation with the start of his new job. It had astounding results. He felt more powerful at the gym. He felt more confident with clients. And he even caught himself flirting with a few of the office girls.
But the worst part of his first week on the job was, undoubtedly, the blue balls.
Juan’s body was not entirely happy when he took away the only release it had known for years. He spent his nights struggling to sleep, and his erections popped up at the slightest provocation. He had to resist the urge to run to the bathroom and jerk off every time he saw one of his female colleagues bend over.
It had paid off, though. After the first week of work, he’d netted a date with Sarah, a cute brunette who worked at the firm. A date! Juan had never dated before, and he had no idea what to expect.
He wasn’t even sure how it had happened, or whether it was a date. He’d mentioned to Sarah that he had nothing planned on Saturday and she invited him out for a drink. He’d fumbled his way to a “yes” and escaped without saying anything embarrassing.
Juan felt like a moron when Sarah came to his “office” on Friday to give him her phone number. How could he forget something like that?
Juan’s “office” was actually a corner room that had been empty before he arrived. He was the last in a wave of new hires, and the firm didn’t have anywhere else to put him. He had a nice view of the city’s train system through the room’s massive windows, but he felt closed off from the rest of his colleagues.
Sarah seemed to like it.
“This view is way better than mine,” she said when she stepped inside. Sarah was about 5 and a half feet tall with curly brown hair. Mousy, but in a cute way.
The room contained three wooden desks, three computers and three chairs. Juan had commandeered the biggest desk only to find his computer excruciatingly slow.
“Yeah,” he said, trying to act nonchalant. “But you at least sit by other people.”
Sarah smiled at him. She wore a tight red sweater and jeans – Juan had learned that, in fact, only the secretaries wore pencil skirts.
“You wouldn’t like that. Everyone who sits by me is old and creepy.”
Juan laughed. He had mostly kept to himself his first week and didn’t know much about the more seasoned employees. Sarah, like him, had been hired recently.
“What’s creepy about them?” He asked.
Sarah folded her arms across her chest.
“They stare at me! I swear to god they pretend to have back problems so they can watch me pick stuff off the ground.”
Juan tried to look concerned. He could hardly blame anyone. Sarah had an ass so round and tight you could probably eat off of it. He’d gone through agony in the shower imagining massaging it, oiling it …
Suddenly Juan snapped back to attention. He could feel himself getting hard. It was too easy!
“Yeah, yeah, that sucks,” he said. He pretended to look for something on his desk. “That’s fucked up.”
Sarah giggled.
“Uh huh…Anyway, here’s my number. I wrote it out because that’s more fun.”
She handed him a scrap of paper and turned to walk away. But she paused at the door.
“Text me if you need anything before Friday night.” She smiled and walked away.
Juan stood holding the piece of paper for a few moments. “Text me if you need anything?” What the hell did that mean?!
A passing train broke his concentration. Juan blinked and pulled his phone out, then started typing Sarah’s phone number in. He was being stupid, he thought. She didn’t mean anything; he was just ridiculously horny and reading too much into the situation.
Sarah’s visit completely destroyed Juan’s focus. He sat at his computer for about 20 minutes wondering whether amatör porno to text her. She, like most of the office, had already gone home. It was 6:30 on a Friday night and Juan only stuck around because he knew he’d masturbate if he went home.
Another hour passed. Juan made plans with a friend to see a movie and tried to read a newspaper to pass the time. But he couldn’t get Sarah out of his head. What the hell would he do on a date with her? Did she even like him or was she just being polite?
“Wow, you must have a pretty good reason to still be here.”
Juan, who had his feet propped up on an adjoining desk and his head buried in an article on city politics, nearly fell out of his chair. A blonde, vaguely familiar-looking woman had stepped into his “office.”
“Are you actually working or just staying late on a Friday for some weird reason?” She asked.
Juan folded the newspaper and brought his feet to the ground.
“Just…just waiting for a friend to pick me up,” he said.
The woman smiled faintly. She had a round face, with thin glasses and a large mouth.
“You don’t have a car? Man, they keep hiring you guys younger and younger.”
Juan cast his eyes at the train stop outside his window.
“Nah, I just…Usually I take that,” he said.
The woman sat down in one of the two open chairs in the room.
“I’m Molly, by the way,” she said. She shook his hand.
Juan smiled.
“Juan,” he said. “Sorry, you just kind of scared me.”
Molly wore a black sweater, black jeans and black boots. Her dirty blonde hair, shoulder-length, and her light green glasses were the only color she had on.
“Me? Nah, I’m harmless. I’ve been here five years and you’ve already got a better office than I do.”
Juan wondered what it was about his office that people wouldn’t shut up about. Molly most have noticed.
“I bet 10 people have already made that joke to you this week,” she said.
Juan chuckled and grinned.
“Try 20.”
The two sat in silence for a few moments. Juan saw Molly look him up and down. She shifted in her seat, then stood and put a hand on the glass door.
“Do you mind?” she asked. Juan furrowed his brow.
“Uh, I guess not,” he said. “What’s up?”
Molly sat back down and started to pick at her chair. She kept eye contact with Juan.
“This is gonna sound really weird, and I don’t know how you’ll take it, and I know you don’t know me and you just started here -” she paused and took a breath. “Juan, can you just promise me this conversation will stay between us?”
Juan was thoroughly confused. What the hell did she want to talk about? Still, he felt a certain obligation to hear her out.
“Uh…yeah, sure.”
Molly took a breath.
“So, before you and the other new people started, a few of us made a bet. A stupid bet, but we were drunk. Very, very drunk. At least I was.”
Juan nodded a few times. Molly couldn’t be older than her late 20s. And she was pretty, in a way. Big eyes, husky voice.
“Anyway, I lost the bet, and the consequences for not following through are very severe. So what I’m about to ask you, and you can say no, is going to sound weird, and I’m sorry. And I really hope you won’t report me because I like working here.”
Molly paused and stared at Juan. He had lost track of what she said and started thinking about Sarah again. Only this time it was Molly’s ass he was massaging, and come to think of it hers was pretty nice, too…
“Juan?”
“What, yeah? Yeah, um, what’s up?”
“Do you want a blowjob?”
Juan, who had been absently twisting the newspaper around in his hands, stopped.
“What?”
Molly looked down, red in the face.
“I said…Jesus. I said do you want a blowjob?”
Juan pushed his chair away from Molly. His face, too, had turned red.
“Why are you – I don’t think -“
“I told you it was a stupid bet!” Molly said. “I’m sorry.”
Juan felt his cock harden despite the uncomfortable situation. She wasn’t serious, right? This was just a stupid bet.
“No, it’s fine,” he said. He managed a weak smile. “I’ve had plenty of dumb bets in my life too.”
Molly tried to smile back.
“No more tequila for Molly, I guess.” She paused. “I’m, um, actually not allowed to leave until you say yes or no.”
“Oh,” Juan said. “Then…”
Molly raised her eyebrows.
“This doesn’t leave the room?” Juan asked.
She smiled.
“Wow. Yeah, Juan, it doesn’t leave the room.”
Juan breathed for a few moments. Surely she wouldn’t really do it, right? And then he’d be the creepy loser who asked her for a blowjob. And Sarah. What if she found out?
“I’m probably the dumbest guy in the world, but I have to pass,” he said.
Molly smiled and turned a deeper shade of red. Juan had the impression he gave the wrong answer.
“Not because you’re not pretty!” He rushed out. “It’s just, ah, I have a date tomorrow, and…ah…”
Molly grinned.
“Wow, what a romantic. Who’s your date with?”
Juan was eminently uncomfortable and wanted to leave. He already anal porno regretted passing on Molly’s offer.
“You know Sarah in client relations? We’re getting drinks tomorrow.”
Molly, however, looked completely at home. She lightly punched him on the arm.
“Wow, charmer. She’s cute. I’m not surprised, though,” she said. “You know, I could actually pick any of the new guys for my bet. But I went with you because you’re the cutest.”
Juan smiled and flushed again. He made a mental note to buy a chastity belt if he had too: His week without masturbation was doing unbelievable things.
“Thanks,” he said. He leaned back in his chair and put his feet up on the desk next to Molly. “To be honest, I’m a little nervous. I’ve never been on a date before.”
Molly picked at her chair again.
“Ah, so you’re a player? Don’t even wine and dine them first?”
Juan looked down. He felt his phone buzz – probably his friend on the way to pick him up – and ignored it.
“Actually,” he said, “no.” He decided to tell Molly the truth – why not? She seemed nice, and they’d certainly broken the ice at this point.
“I’m a virgin,” he said. He waited for Molly to react.
She did. Molly smiled and moved forward in her chair.
“Oh my god, are you serious?” She asked.
Juan huffed.
“You think I’d lie about that?”
“Good point. Wow, I never would have guessed.”
Juan was exhausted. In one day he’d had two conversations with gorgeous girls he never would have thought possible. He needed to go see his friend, destroy his brain with a crappy movie and hit the gym before bed.
“Yeah, anyways, Molly, it was nice to meet you. And I won’t tell anyone about the bet or anything, but I should probably go.”
Juan stood and crossed the room to open the door and show Molly out of his “office.” But she stopped him with a hand on his leg.
“Wait, Juan.”
He looked down at her.
“You have to let me blow you.”
Juan stepped back.
“What?”
Molly remained completely calm.
“Juan, take it from someone who knows. No offense, but Sarah is not gonna want a nervous virgin taking her out tomorrow night.”
Suddenly she stood, matching Juan’s six-foot height. She whispered in his ear and stroked his right leg.
“So let me suck you off and relax you a little bit.”
Juan fought the urge for about three seconds. That’s how long it took his cock to completely overpower his brain.
He leaned in to kiss Molly and she pulled back. She put a finger on his lips.
“No,” she whispered. “You have a date, remember?”
Juan smiled. He felt his cock growing in his khakis.
Molly pushed lightly on Juan’s chest.
“Sit down,” she said.
Juan did as he was told. Molly ran her hands down his chest and legs as she knelt on the floor in front of him. She slowly unbuckled his belt and unzipped his pants.
“No one ever has to know,” she said. “In fact, I think I’ll swallow all the evidence.”
Juan almost came right then. Molly’s half-lidded smile was too much for him. And she was going to swallow?
He lifted his hips slightly and pulled his pants down as Molly watched on her knees. Juan was already rock-solid, and his cock pushed against his briefs.
Then a horrible thing happened.
“Oh my god, Juan. Are you serious?”
Molly had stopped. She had both hands over her mouth.
Juan’s cock shriveled instantly. His worst fear had come true.
“I’m sorry,” he said. “I’m really sorry. I should go.” His face crimson, Juan stood to pull his pants back up.
Molly, who had started laughing, grabbed his leg.
“No, no, Juan. I’m sorry.” She snorted again. “It’s just -“
“It’s just fucking small! I know!” Juan yelled.
Molly only laughed louder. She was cackling at this point, rolling around on the floor.
Juan had managed to pull his pants up. He started to buckle his belt.
“You don’t have to laugh, Jesus.” He said. His week had just gone from amazing to pathetic. Juan wanted nothing more than to go home and masturbate – it was what he needed.
Molly’s laughter subsided.
“Wait, Juan, wait,” she said. “Do you really not know?”
Juan buckled his belt and started grabbing things off his desk. He didn’t need this. God, is this how Sarah would react?
“Know WHAT?”
Molly covered her mouth again. Her eyebrows shot to the top of her face.
“Oh my god,” she whispered. Then she spoke louder. “Juan, your cock is fucking huge!”
Juan paused. He furrowed his brow.
“Really?”
Molly was still on her knees. She nodded, smiling.
“Juan, I’ve never seen one that big. I’m serious.”
Juan slowly slid back down into his chair. He set his things – phone, building access card – back on his desk. He looked at Molly.
“Really?”
She slapped his leg.
“Yes, really, stupid. Oh my god, I can’t believe you don’t know! Don’t you, like, watch porn or anything?”
Juan didn’t. His own imagination had always been enough – save for the Fleshlight incident. He grinned.
“No.”
“Wow, you ana breakers porno must be one in a million,” Molly said. She put a hand on his shin. “Okay, before I was doing you a favor, but I really want to suck your cock now, Juan.”
Juan’s cock stirred. He smiled down at Molly, the gorgeous blonde on her knees for him.
“If you’re really not kidding about this…I mean, go ahead,” he said.
Juan pulled his pants down again. He moved to do the same with his briefs, but Molly gently placed a hand on his.
“No, no, no,” she said. She put both of her hands on his hips. “Mine.”
Juan watched Molly slowly pull his briefs down. Her face was so close to his groin that his cock lightly slapped it when she let it free. Molly giggled. Juan almost exploded when he felt her breath on his meat.
“God, I just want to stare at it,” she said. And she did. Juan’s cock towered over Molly’s face, throbbing with urgency.
Molly smiled up at Juan.
“Is it wrong that I want to measure it?” She asked. Juan smiled.
“Uh, feel free,” he said. Molly jumped up, startling him. She ran from the room.
“Back in a sec!” She yelled over her shoulder.
Juan suddenly felt very exposed. He heard his phone vibrate on his desk. Sure enough, he’d missed two calls and two texts in the past 10 minutes. He hurriedly dashed a message to his friend.
“Getting head not kidding tell you later”
He set his phone back on the desk and waited. Was this really happening? Was a pretty blonde woman about to suck his cock? Juan’s head swam.
He waited another few minutes for Molly to return, out of breath and clutching a green plastic ruler.
“Sorry,” she said. “It’s a little harder to find one of these than I thought.”
She walked slowly back to Juan and leaned over him, speaking softly in his ear.
“I see you haven’t lost interest.”
Molly sank back to her knees and rubbed the ruler between her hands. Juan, impatient and horny, gave her a puzzled look.
“So it’s not too cold on your skin,” she explained.
Juan wondered how many times Molly had done this before. Then he felt her grip his cock and lost all thought completely.
Juan could only stare as Molly squinted at the ruler. She smiled.
“Eight and three quarters of an inch,” she said. “Sarah will be very happy.”
Juan held onto that number. Almost 9 inches. He wondered why he had never thought to measure his own cock before. Or why he always assumed it was too small.
Molly set the ruler down on the floor next to Juan’s left foot. She sat up, putting both her hands on his thighs.
“Now, the main event,” she breathed onto his balls. Molly looked up. “I don’t expect you to last long, but just take deep breaths, okay? I need to take my time here.”
Juan followed instructions, forcing himself to breath deeply. It helped calm him for a few seconds. Then Molly wrapped her lips around the head of his cock.
“Ohhhh,” Juan groaned. Twenty-two years of waiting had just paid off.
Molly sucked lightly on Juan’s cock head. She couldn’t believe what she was doing, but a bet was a bet. And, she had to admit to herself, the second she saw the monster Juan had, the bet no longer mattered. Molly liked sucking cock, and Juan’s was perfect.
So she treated it well. As Juan watched from above, Molly bobbed up and down on his cock head, letting rivulets of spit run down his shaft. She pulled back and jerked him with one hand, spreading her saliva across his meat to lubricate it.
Juan was an expert masturbator, and he’d learned how to regulate himself long before that night. Not even a week’s worth of pent-up arousal could force him to completely lose control, though it didn’t help. He breathed deeply and tried to imagine Molly’s work as nothing but a particularly good version of one of his own sessions.
But Juan never talked dirty. Molly apparently did.
“I always say a good blowjob is all about spit,” she said. She was still pumping his cock with one hand. She looked directly into Juan’s eyes and spat on the head of his cock, lubing it up even more. “Your cock looks so fucking good, Juan.”
“Ahhhh” was the only reply Juan could muster.
“I wonder how much I can fit in my mouth?” Molly said. She stopped moving her hand, but kept it firmly gripping Juan. “Want to watch me try the whole thing?”
“Uh huh.”
Juan had closed his eyes. He felt Molly remove her hand. Then, a few seconds later, he was in her mouth.
The blonde beauty bobbed her head on the first four inches of Juan’s cock, dripping still more saliva as she went. Her mouth felt like heaven.
Molly pursed her lips around Juan, gripping his cock tight. She moved faster, moaning around the fat dick in her mouth. The vibrations caused a sharp intake of breath above her.
Slowly but purposefully, Molly forced more of Juan’s meat into her mouth. After a few minutes of drool and hard work, she had seven inches inside her. Juan had thrown his head back and jammed his eyes shut, but he risked a peek at the sight below him.
It didn’t disappoint. Molly expertly plunged down on his dick, shoving her face into the last of his mammoth. She hadn’t throated the whole thing yet, but she was getting closer. Juan’s cock was covered in her spit, and more spilled out every time she slowly drew off to lick the head. His balls and the chair below them sat in a pool of her juice.
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