The Rich Nerd and the Broke Blonde Pt. 01

Anne watched Wesley Tillman walk in. He was always pensive, eyes cast down and shifting every now and then, eyeing the corner as he closed the door.

Won't he ever relax? They have been at this for a month now. Anne shook her head and got up from her chair. He was tall and gangly, with black curly hair. Whenever Anne thought of Wesley Tillman, two thoughts come into mind. Firstly was his broad rimmed glasses that made him look every part of the nerd that he was. And secondly and most importantly to Anne, he was loaded. He may not look like it with his tucked in polo and khaki pants but his parents were richy rich!

Both of them were seniors, Anne remembered getting invited on Wesley's eighteenth birthday at his house. No, not a house, the place was a mansion! They had a big ass pool, Anne remembered seeing a Ferrari on the driveway. Oh, and a maid and butler! A real live maid and butler! She heard rich people had them but never actually saw them.

And what did Anne get for her eighteenth birthday? A thirty dollars gift certificate and a small homebaked cake. She had to lie to her friends and make up an excuse to her mother why her friends aren't coming. It was embarrassing.

"You made sure you weren't followed?" Anne interrogated him, moving closer. She had to scrunch up her nose as because he might as well have emptied an entire bottle of body spray on their meet up.

"N-No! I-I made sure, okay!" he stuttered.

"Whatever," Anne said. "You do have my money, right?" she added. He only nodded.

But there was something strange in his eyes, like a sadness in them, kinda reminds her of a puppy. Still, he didn't stop her from unbuttoning his jeans.

The first few times they did this, his groin was unshaved. She didn't mind but every now and then a pube would make its way somewhere in her mouth. She remembered saying something about it. A week later, she found he had shaved and he had always shaved since whenever they go for their meet.

His limp dick was a good three inches long. Asleep and soft.

He drew a sharp breath when she grabbed hold of it.

Some twists around the block, the sound of traffic, horns honking and cars passing echoed in their secret meeting place. It was an old locked up shop, the display window boarded and the way to get in here was a path so narrow, you had to walk sideways to fit.

It was the perfect hook up spot and they were the only two who knows of it. Anne found the spot where she could just hang, maybe take a smoke or two. When she made this proposal to nerdy Wesley, this place was the ideal spot.

His groin was smooth to the touch, almost like a baby's, Anne had to keep herself from laughing.

"W-what?" he asked.

"Oh, nothing."

She began stroking his cock with her thumb and index finger. He was breathing through his mouth and his glasses kept drooping down whenever he tried to look down on her. One hand fondled his balls, gently feeling through his sack.

She opened and wide and made sure to look him in the eye as she put one ball into her mouth.

"Oh Anne!" he exclaimed.

"Hush!" She hissed at him. No one was going to hear them. But Anne liked to be in control here. She likes to be the one holding the balls. Literally. He gripped the rack closest to and grip it so tight his knuckled turned white.

His face scrunched up in ecstasy and pleasure as Anne put her lips and tongue to work. She suckled on his balls like a baby with a candy, passing her tongue this way and that. He couldn't help but let out some groans under her ferocious attack.

"OOOHHH!! ANNNE!!"

His grip tightened.

"Oh Anne! Can I- -"

"Quiet!" She hissed at him again.

"Can I grab your head please?"

"No, not yet," Anne stroked his manhood. Slowly feeling every bulging vein, the little beast slowly rose, filling out the spaces in her grip. It stood slightly crooked and a decent seven inches long.

"..My God, you're great." Wesley said.

It's not like he was getting it from anyone else, Anne thought.

She draw her hair back to her ears, tucked them in and gobbled down the head, just the head.

His breathing came in rasps. His gripped it so tight, his knuckles turned white.

She released her mouth, fingers still stroking his erect manhood.

"Relax, will ya? The more you tense up, the faster you'll cum." Anne had to ensure that the experience would left him craving for more, had to keep him coming back and give her his money.

"I can't help it." He rasped.

Anne shook her head, after all this time the nerdy bastard still lacks experience. She eased up on her hand job slowly holding down the base of the shaft. It twitched rythmaticly.

"Catch your breath and uncurl your toes. Loosen up, you know," Anne suggested.

She still gripped on the base of the shaft. Anne watched Wesley. He didn't look her in the eyes. His eyes was shut in ecstatic pleasure. His took deep breathes of air till his breathing relaxed and his shoulders loose.

Anne felt his cock loosen up a bit too.

And she went back to work, slowly jerking his engorged manflesh.

When he was getting used to her rhythm she looked to her phone, they've been here for twenty minutes. Time to make a home run.

"I'm going fast and hard now, you ready?" Anne asked.

He didn't mutter, only a stuttering nod of his head.

"..Y-Yes Please," he finally managed.

She opened her mouth and slowly forced his cock in, her tongue soothed the base of his cock as it slid down her throat. Slurping noises, messy sounds went about as she worked her mouth, the sound of saliva lathered on his cock with her tongue. She found his hands on her head grabbing handfuls of her hair.

They didn't hurt as much. But when you have your entire cock inside someone's mouth, it must've work wonders for guys.

"Auughh!" Wesley groaned.

She pushed till she could slightly feel the tip of it at the back end of her mouth.

Anne gripped his bare thighs and slowly resisting working her tongue within his flesh till it slid out.

His breathing came in fast and Anne's hands were a blur,

"OH! Oh Anne! I'm Cumming!"

She outstretch her tongue and opened her eyes. She found that he really loved it when she looked up into his eyes.

"Auugh!"

He came a load on her face. Anne had to close her eyes. Stings like a fucker when cum gets in your eye. Wesley the nerd was reeling in from his explosive climax, he had to lean against the old counter behind him. His penis was bare and his khaki trousers down to his ankles. He was catching his breath from all the excitement Anne gave him.

Then once more it became a routine. It did not take five minutes for themselves to clean up. Anne forgot to bring tissues.

"Crap," she said to herself and shrugged as she used her fingers to wipe them clean. She wiped her cum encrusted fingers against some walls. She really needs to bring some tissues next time.

What happens here, stays here. And he's good on his word. Anne made sure of that.

He took out his wallet. Sweat glistened on his forehead, but otherwise none would know the better that he had just his cock sucked by Anne. He would go one way and she another. And let anyone none the wiser.

He took out a crisp hundred and put it in Anne's hand. Then he muttered to himself and took out some ones and added them.

Anne quirked an eyebrow but she kept her mouth shut. She didn't mind more money.

She took a mirror she hid around a drawer in the old counter. It'd be a hell of a day if she had to explain to anyone why there's semen hanging somewhere around her.

"Hey uhm, Anne"...he started.

"So uhm...Anne, listen..." He stuttered while cleaning himself up. He took a deep breath and looked her in the eye. There was something off about him today.

"Hey, I was wondering if I could invite you to some food out sometime - -"

"No." Anne interrupted.

"We made a deal remember. You pay me money and I give you blowjobs right. You get off, I get rich. No need to complicate things. And...No offense but you're not my type." Anne simply laid it out. She thought that this might happen, that dear sweet Wesley would eventually get...emotional.

"Oh...Okay. I guess," He scratched his head, looking down on his shoe.

"So, see you next ti- -"

Anne didn't let him finish, turned her back, counting her money and was off the door.

***Author's Note:

Thank you for taking the time to read my work. I'm just an amateur writer and would like to hear your thoughts about the story. I know I still have plenty to learn and improve. Thank You.