“Hey there, Cherry Pie… How’s business?”
Cherry furrowed her brows and turned toward the man addressing her. Her mouth was prepped to spew forth a string of expletives, but instead lifted into a bright smile.
“Oh, hey,” she called out to the handsome young man crossing the street to meet her. “I’m off duty right now.”
The nighttime street- glistening from an earlier rain and the streetlights- was completely dead as nineteen year-old Cherise Davidou stopped, her purse slung over her shoulder. She had just gotten off work at the coffee shop and was on her way home for a quick shower before heading to her
next
job.
“Oh, I’m sorry,” Jacob said sarcastically, playfully, as he jumped up on the curb. “With
that
little getup, I figured you were hunting.”
Cherise- or
Cherry
to her customers- glanced down at her outfit and mock-grimaced. That night she was wearing her low-rider jeans and a tight, red cami with no bra. The tips of her shapely 36C breasts poked though the material, courtesy of the night chill.
She looked back up and tossed her auburn hair off of her shoulder. “
Everything
I wear turns you on, baby.”
Jacob smiled warmly and opened his arms. They pulled into a tight embrace, and he kissed her cheek. “So, are you busy tonight?” he whispered into her ear.
She gave him a good squeeze and pulled away, readjusting her purse strap. “Nope,” she said, shaking her head. “You’re in luck.”
Jacob and his wife, Cassie, had been part of her
selective
clientele for a little over six months. Being a college freshman, trying to pay her way through school, she had a small group of discreet and carefully-chosen people that she sometimes
performed favors
for. The money earned from these favors was fairly good, with most of her customers part of a group of friends who were comfortably wealthy. The only problem was that most of them were also well-acquainted with the Dean of Haughton College, Mr. Thornton.
Most of them were very friendly and would never tell Dean Thornton. Jacob and Cassie Farrell were part of that group. There were, however, a few that enjoyed the leverage they held over her and used it to their advantage. Hillvale was a relatively small town, and news traveled quite fast. Cherry had to be very careful, going along with the requests and commands of those who wouldn’t hesitate to tell her secret.
“Why don’t you just come on over, and you can shower at the house,” Jacob offered.
Cherry smiled and nodded. “I really wasn’t looking forward to taking those steps anyway.”
The boarding house she stayed in- although cozy and quiet- was four stories, and her room was at the top. She’d lived on campus for a while, but when she began her favor-giving excursions she knew she needed a different place.
The two of them walked silently but briskly across the street toward Jacob’s Camry. She’d been in that car more times than she could count, and she loved the way it smelled. She loved sitting next to Jacob- who, at the vibrant but mature age of 31- was strikingly good-looking and well-built. He taught physical education at the high school, where his wife just happened to teach Senior English. They were independently wealthy, having inherited their country home and surrounding land- in addition to a hefty bit of money- from Cassie’s late parents. Cassie- who was 27- had grown up in Hillvale, briefly moving to New York when she married Jacob, a native of Albany. When her parents were killed in a car wreck a couple years before, they’d moved back and gotten on at the school.
Cherry thought the world of them both, but it was Jacob who she especially enjoyed spending time with. Aside from his voracious but generous sexual proclivities, he was an extremely easygoing and fun-loving man. They had conversations about a multitude of things during their rides to the house on the outskirts of town, and he always made her laugh.
Though it was strictly off-limits as part of her casual deal with the Farrells, sometimes Cherry gave Jacob a small preview of what was to come in the car. Cassie had expressly forbidden any type of sexual activity between Cherry and Jacob when not in her presence, but every now and then the two of them would give in to their desires and break the rule. Most often it would start out with Jacob rubbing her thigh as he talked. From there it would escalate to him rubbing her pussy through whatever she was wearing, and the feel of his hand on her just drove her insane with lust. He would make a deal with her- she would suck him off as he drove down the long road that led to the property, and if she swallowed his cum, he promised her some extra cash when Cassie wasn’t looking.
She could tell that night’s drive wouldn’t be one of those special ones as they fastened their seatbelts. She was in a particularly lustful mood, and she licked her lips frequently, a silent signal that she was willing to give him head. He did not make a move, though, as they drove down Main Street. He frequently looked through his tinted windows, indicating to her that he’d met someone he knew on the way to her place.
He wasn’t so nervous that he couldn’t converse. “Cass bought a new dildo Saturday night,” he said, amusement in his voice. “It’s a huge, hunking thing.”
“Really?” she asked, an interested lilt to her voice.
He nodded. “All she’s talked about is using it on you.”
Cherry chuckled. “She’s saving it for me? Aww…”
Jacob chuckled. “Yep. She just won’t shut up about it, Cherry Pie. She’s been constantly describing how she wants to stick it in her mouth and fuck you with it.”
“Mmm…” she moaned, shifting in her seat.
Cassie was a very pretty woman, very feminine and fit. She had long, raven hair that she always wore down, relishing the appreciative looks she got from the men in town. Her breasts, though not as ample as Cherry’s, were high and proud and capped with large, thick brown nipples that Cherry loved to suck. She had a trim little waist and a firm little ass, and she looked extremely hot in a pair of jeans and a tube top. The vision of Cassie’s exotic mouth wrapped around a dildo, pumping Cherry’s wet pussy with it, really got her juices flowing. She imagined Jacob laying underneath her as she rested on all fours, licking her swollen clit as she hungrily sucked on his 8-inch cock.
She sighed and leaned back in her seat. “I can’t wait.”
“Me, either,” Jacob said huskily, gripping the wheel a bit tighter. “I had to lock myself in the bathroom this morning, thinking about that tight little puss of yours.”
Cherry laughed. “Whatever will you guys do when I graduate and move away?”
“Buy a lot of plane tickets, I guess,” he chuckled.
The rest of the drive was nice, the radio playing seventies easy rock. Feeling mischievous, Cherry occasionally reached over and brushed her fingers over the bulge in his pants. She was even so bold as to offer him a handjob, no charge. He just playfully smacked her hand away from his obvious erection, telling her to be patient.
They pulled into the driveway and slowly made their way down to the garage, Jacob’s erection standing out against the bottom of the steering wheel through his shorts. As they pulled into the garage, she caressed his cock one last time. He placed his hand over hers and jerked himself a few times before cutting off the engine and unlocking the doors.
Cassie was waiting inside the door, in the spacious kitchen. She had just finished up the dishes, and looked incredibly sexy in a pair of snug jeans and a tank top. Her long tresses were pulled up in a messy bun, and Cherry fought the urge to yank those shiny locks free as the two women embraced.
