Hilly and Ben – Their First Date 4 [mf][Str8][oral][mast]

Click on my name for the previous story called The Choir Trip or the first three parts of this story.


"Oh look," Kaylee snarled. "It's Ashley and her mini-me."

Bailey laughed like the joke was funny. The two of them sat at the center of attention in the soprano section surrounded by their venue of vultures. Hilly had been similarly insulted by the pair when she arrived but chose to ignore them to get her music together for rehearsal.

Looking up, she did notice something different with Ashley and Madison. Hilly remembered that Ashley had driven Madison home after the student council meeting. Thinking of her own study session with Ben, she smirked and wondered if they made use of their time together as well.

Ashley looked over to gave Kaylee a snort and look of pity. "Is that all you got, Bi-Bitch?"

It made Hilly chuckle that she dropped their new name for the duo in front of the whole choir room.

"Bi-Bitch?" Bailey sputtered.

"Two bitches in one," Ashley explained as she passed them by.

"The only thing bi I see around here is you," Kaylee said with a wicked grin, like she was telling a deep, dark secret.

Hilly and Ben – Their First Date 3 [mf][Str8][Mdom]

Click on my name for the previous story called The Choir Trip or the first two parts of this story.


Hilly sat down in Ben's car with a rumble of anticipation in her stomach, then Ben shut her door. He danced around the front of the car with an eager grin. After he opened the driver's side door and plopped down next to her, he said, "Ready to study some algebra?"

She leaned back against the door and put her fingernail between her teeth to give him a coy look. "Drive fast."

The previous evening had been a blur of homework and safety class research with a few breaks in between to introduce Ben to Violet over a video call. After she told him all about her little purple friend, she decided at the last minute to keep her study plans a surprise.

During the day at school Hilly kept teasing Ben with kisses and secret touches. His frustration had him waiting by her locker at the end of the day to lead her to his car. He'd held her hand and carried her books for her, making her feel like one of the girls in the old romances her mother read.

Hilly and Ben – Their First Date 2 [mf][mast][toy]

Click on my name for the previous story called The Choir Trip or the first part of this story


Stepping back into the choir room that Monday morning was harder than Hilly had imagined. She was no longer the little wallflower she'd been on Friday and the glances she got had a weight of judgement in them she'd never felt before. Her first impulse was to run over to greet Ben, but that felt like hiding in a way. Instead she stepped more confidently than she felt toward her section where Kaylee and Bailey were holding court.

"Morning," Hilly said brightly as she joined the group and put her book bag under her chair. The choir room was a shallow semi-circle of rising rows with walkways between each voice section. Because of her short stature she sat on the front row. A circle of other sopranos were standing around Kaylee except for Madison, Ashley, and a few others chatting quietly on the back row.

"My mother nearly put me in rehab because of you," Kaylee growled. Madison and Ashley both frowned at her when she spoke.

Hilly and Ben – Their First Date 1 [mf][mast]

Click on my name for the first part of the story: The Choir Trip


Hilly tossed her bags from the choir trip on her bed and looked around her room. There were posters on the walls for bands she didn't listen to anymore. The furniture was still the curvy white and pink bedroom set her parents had bought when she was five. It was covered with stickers from cartoons and games she'd once loved. Even though she'd only been gone for three days, it felt like a stranger's room.

"So tell me all about Ben," Rose said as she quietly shut the door. The tone in her mother's voice was a mix of excitement and fear. When Hilly didn't answer right away, Rose studied her face more closely.

"He's a nice guy from choir who's going to tutor me in algebra."

Rose didn't look like she bought it. "When I was your age there was an older guy I was head over heels for. We dated for a while, but he wanted to do things I wasn't ready to do."

"I'm ready to understand algebra, Mom." Hilly tried hard to keep the impatience out of her voice.

Hilly and Ben – The Choir Trip 5 [mf][mast]

Click my name for the previous parts of this story.


Hilly dragged her bags into the banquet room for breakfast with a satisfied smile on her face. Even being on couple of hours of sleep couldn't keep her spirits down. Madison was a little more subdued, but even she wasn't immune to Hilly's good mood.

"Thanks for helping me with my hair this morning," Hilly said as they put their bags down with the others. She had woken up late with horrible bed-head after going to sleep with wet hair. Madison had brushed it out and put it into a French braid right before they came down.

"Anytime." Madison put her own bags down with a sad smile and stretched out her back. "I'm gonna sleep all the way home."

"Me too," Hilly said as she yawned. Her back and leg muscles were hurting so much she'd taken a pain reliever. There was nothing she could do about the soreness she felt inside as she walked to the breakfast buffet line, but it did serve as a reminder. I'm not a virgin anymore.

Hilly and Ben – The Choir Trip 4 [mf][Str8]

Hilly woke wrapped in Ben's arms. She checked the clock on the night stand and smiled when she saw they'd only been asleep for an hour. It was barely Sunday and there was still plenty of time to find something productive to do with those last two condoms.

When she heard Ben sigh in his sleep, she began to kiss him awake. It didn't take him long before he squeezed her tight in his arms to hum against her hair.

"Not too sleepy?" he whispered.

"I told you I'm not wasting this night," she teased. She rolled over on her side and pressed her ass against his thickening shaft. "Can we try this way?"

"On our sides?" he asked as he reached for the second condom. "Will it work?"

"I don't know," she giggled. "It'll be fun finding out. I just want this time to be slow and relaxing."

Ben prepared himself with the second condom, then tugged her hips along the sheets to reposition her. He slipped one arm under her neck and placed his other hand low on her stomach to pull her closer.

Hilly and Ben – The Choir Trip 3 [mf][first][slow]

Hilly and Madison walked into the banquet room reserved for the choir members to eat breakfast and rehearse. The room had seven round tables with eight seats each, about half of which were occupied by students and chaperons. The buffet line along one wall was currently empty, so they got in line before the rest of their group came along and pillaged the food.

"I still can't believe you and Ben are going out," Madison said as she scooped some scrambled eggs on her plate.

Hilly just smiled and glanced over at Ben. He was saving them spots at his table with some of the other guys in the tenor section. She still hadn't given Madison any details, but she did mentioned that Ben had made it perfectly clear they were an item.

"God, if looks could kill," Madison leaned in to whisper.

The terrible trio were whispering together while Kaylee glared at Hilly. Since Kaylee was the section leader for the sopranos, Hilly was going to have to deal with her attitude for the foreseeable future. Remembering what she and Ben had together made it easy to laugh her off for now.

Hilly and Ben – The Choir Trip 2 [mf][mast][oral]

Click my name to see the first part.


When Hilly used the cardkey on her hotel room door, it flew open as she pushed making her fall on the floor. "Fuck."

"There you are!" Madison helped Hilly up, then grabbed her garment bag and shook it out flat. "I was worried when I didn't see you on the bus."

"I'm too short," Hilly said as she tossed her duffel bag on the far bed and yawned. "I could barely see the movie over the headrest in front of me."

Hilly didn't have many girl friends after growing up with three brothers. She found the catty games most girls played hard to deal with, but Madison was so easy going they'd hit it off and never looked back. Their only real difference of opinion involved sex. Madison claimed she had no interest at all, but always wanted to know every detail of Hilly's tame adventures.

"So did you sit with Ben?" she sang.

Hilly schooled her face, but could feel the heat rising. "Yeah. He's nice."

"That blush says he's a little better than nice."

Hilly and Ben – The Choir Trip 1 [mf][mast][oral]

Hilly wasn't very tall and she still had the spotty complexion of an adolescent. The square glasses she wore made her soft brown eyes appear larger and her long brown hair often needed to be brushed out. Her bright smile and bubbly personality made most people think she was younger than she actually was, even though she had the firm breasts and full hips of a woman. But she wasn't a woman. Not yet anyway.

She loved the attention she got when she sang, so she auditioned and won a place in the school choir. The choir spanned all ages, giving her the chance to tease the older boys. She had discovered her charms worked even better with them than the skittish boys her own age. She would tell them risqué jokes she'd learned from her two older brothers and made sure to smile to encourage their attention.

It was all in fun, she told herself. Their kisses were exciting and when she allowed them to touch her breasts it made her knees weak. But she didn't really understand her power over them.