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.
Rose nodded and suppressed a grin. "Give me your laundry and I'll get it started for you."
When Rose reached for the bag, Hilly dropped her chin and gave her mother a withering look. "You've made me do my own laundry since I was ten. What're you tryin' to get a look at my dirty clothes for? What's really going on?"
Hilly knew her mother well enough to know she'd never ask about sex directly, despite her willingness to share advice on how to avoid trouble. Their puberty talk was still a barren desert of mutual embarrassment and her first period had been a tearful disaster. But that wouldn't stop Mom from snooping in Hilly's dirty clothes for the evidence to answer her unasked questions.
"I don't like your attitude," Rose frowned.
"If you want to know something, just ask." Hilly let the challenge ring in her voice.
Rose turned back and crossed her arms under her breasts. "You've never talked about bringin' a boy home before. He's got to be two years older than you. Your hair is up in a French braid. And suddenly you're wearing makeup. What's really going on?" she asked, mocking Hilly.
The heated accusation in her voice didn't match the silly list and question she asked. It took a real effort to keep from rolling her eyes, but Hilly managed to keep a straight face when she said, "You're going to be a grandmother."
"What?" Rose whispered as she put her hand over her mouth.
"Just kidding. He's going to tutor me in Algebra." Hilly turned back to the bed and began to sort her dirty clothes.
"Hillary Rose! What's gotten into you?" Her mother's overwrought tone made Hilly smirk.
About seven inches of Ben Meyer. Keeping her expression neutral, she stared at her mom as she dumped her sorted clothes back into her dirty clothes hamper. "When the police came after I knocked out the guy who drugged Kaylee, Ben stayed with me the whole time and just held my hand."
"That was nice of him." Her mother had a skeptical expression.
"He is nice." She lifted the hamper under her arm. "You'll see."
Rose sighed and opened the door to leave. "I'd better not be a grandmother for at least another ten years."
With her mother's inquisition over, Hilly left Rose in the kitchen to go into the laundry room between the kitchen and garage. She glanced back to confirm her mother was occupied before grabbing the stain spray.
All my underwear are wrecked, she thought with a secretive smile as she sprayed the gusset of each pair. Ben had kept her in a constant state of arousal the whole trip and her Mom would've had a fit if she'd seen the crusty evidence.
Hilly put her bras in the knit bag that kept them from getting ruined in the wash, then dumped her remaining clothes in the churning water. Ever since she'd been doing her own laundry, she avoided white fabrics and delicate materials that required special handling. It was easier to just do one big load instead of having to do multiple smaller ones. Now she found herself dreaming of the kind of soft satin panties and silky bras Madison usually wore, no matter how much extra effort it would take.
Closing the lid of the washer, Hilly made the decision to class up her look a little. As she walked back to her room, Hilly considered her style. For years it had consisted of denim, cotton t-shirts, sweats, and casual tops. If she needed to dress up or wear a skirt, she'd borrow from Madison or her mom. The reaction she'd gotten by dressing up on the choir trip made Madison's point that it didn't hurt to make an effort sometimes.
Thinking of Madison reminded her of the odd scene at school when they got off the bus. She couldn't just say, Hey, Madison, I'm sorry I just realized you had a lesbian crush on me all this time. I'm not interested, but I'm totally cool with you and Ashley dating or whatever. But that's still sort of what she needed to say.
Hilly had no physical attraction to Madison or any other women, but the idea of Madison not being her friend anymore made her chest hurt. That was when she realized now how bad it must have been for Madison seeing her with Ben. It was crazy how complicated everything had become.
She looked around her cluttered room and made another decision. First, she began to take down the old posters and rolled them up on the bed. Then she started removing the old dolls and toys she hadn't played with in years and put them on the bed as well. Lastly, she went through her drawers and closet pulling out clothes that were too small or she knew she'd never wear again. In less than an hour the last vestiges of her childhood were piled on her bed. Then she heard someone sigh behind her.
"So is it true?" Shane asked as he leaned against her doorway.
Her next older brother, and the person responsible for her being called Hilly instead of Hillary, stood looking at her with an inscrutable expression. At two years older than she was, he had become a thinner, younger version of her father topped with her mother's curly brown hair.
"Are those empty boxes still in the garage?" she asked, ignoring his question.
"Yeah," he said. "And I'll get 'em for you if you tell me what's going on with you and Ben Meyer."
Hilly looked him straight in the eyes. "He's gonna tutor me in algebra."
"I heard something else went on this weekend."
"From who? Nathan Alexander?" Hilly rolled her eyes. "He's still pissed because I won't let him kiss me anymore."
"Wait, you kissed Nathan?" Shane stood up straight and got a tense look in his eyes.
"Why do you even care?" she asked as she pushed past him. "Never mind, I'll get the boxes myself."
She stalked through the house to the door out to the cluttered garage. The family hadn't been able to park a car in there for years, but it was still fairly well organized due to her mother's persistent influence and regular punishment work details when the kids screwed something up. Hilly found the folded packing boxes and box tape near her father's workbench as Shane appeared in the doorway.
"So when did you start kissing older guys?" Shane demanded. "Nathan is my age just like Ben!"
"As soon as I figured out the boys my age think kissing is all about cramming their tongues down my throat, I tried out some older guys." Hilly shrugged away the embarrassment, but refused to let her brother see it. "Like you never kissed Mindy Sanderson at our church lock-in last year?"
His mouth snapped shut. "How'd you know about that?"
"Unless you want everyone to find out just how much I know about you, I suggest you keep what you think you know about me to yourself." And I'm gonna rip Nathan Alexander a new one on Monday.
Hilly left him to close the door to the garage as she carried the boxes back to her room. She knew dating Ben was going to be hard, but she'd hoped to have more time to prepare herself. Shane followed her back to her room to watch from the doorway again.
"What are you doing anyway?" he asked an impatient tone.
"I'm changing my room around." Hilly wished she could get new furniture to update the little girl feel it had. First to go were the items she put on the bed: posters, stuffed animals, dolls, a last few toys, and clothes she knew she wouldn't wear again. After she filled one of the boxes, she taped it shut to slide it towards the door. "Make yourself useful and carry this to the garage for me."
"Fuck off. Do it yourself." Shane stomped away and slammed the door to the room he shared with her younger brother Pete. She knew Shane couldn't wait for Charles to leave for college in the fall so he could have his own room. Pete was still young enough to be into toys and never picked up after himself, which was always a source of tension between the two of them.
Hilly carried the first box through the house and into the garage until she had time to take it to the donation center. When she passed the washer, she took the clean clothes and put them into the dryer. The net bag she emptied, removing her bras to hang over the bathroom shower rod to dry.
While she was still hanging them in the bathroom Charles came rushing in, then stopped to stare at the ceiling. "God, do you have to hang those things in here?""
Hilly looked over her shoulder at her oldest brother with a grin. "Why? Does your little sister having boobs bother you?"
"I liked you better when you wore Shane's hand-me-downs and tried to fight me all the time."
"Everyone grows up," Hilly said taking her time to untwist the straps. Ben had opened the center clasp on the beige pair when he kissed her breasts for the first time. Remembering built up a warmth in her stomach as she caressed the soft cups.
"I gotta pee," he grumbled. "Are you done yet?"
She punched his shoulder on the way out of the bathroom. "I'll lock the door for you," she said as she pushed the button on the doorknob and pulled the door shut.
When she returned to her room, she closed the door, sat on her bed, and pulled out her phone. It was time. A swipe and two taps later the phone was ringing.
"Hey." Madison didn't sound especially happy to hear from her.
"Sorry I slept the whole way home. I didn't mean to totally ditch you."
"It's okay," she sighed. "Ashley kept me company."
Hilly burned to just lay it all out, but couldn't read Madison well enough over the phone to guess how she'd take it. She decided to play the angles instead.
"You know, Ashley seems pretty cool once you get her away from Kaylee."
"Yeah, she's nice," Madison agreed. The warm tone in her response reinforced Hilly's perception of them liking each other.
"Maybe she could hang out with us sometime," Hilly said. "I know she's older and all, but I wouldn't mind." That must have been a bit too much because Madison sighed instead of answering. "You okay?"
"I need to tell you something. But when I do you may hate me," she whispered.
"Maddy, I will always be your best friend. Nothing will ever change that." Hilly held her breath and closed her eyes.
"I think I'm gay." The tense whisper communicated her hesitation and fear.
Hilly grinned slowly. "I will always be your best friend," she repeated as gently as she could. "That changes nothing."
"Did you know?" Madison asked with wonder in her tone.
"I'm a little dense, but I think I figured it out when Ashley looked back at you this morning. She had the exact same expression I've seen on Ben's face lately." Madison's chuckle made Hilly relax against her headboard. "If you're happy, I'm happy for you."
"We talked the whole way back. She told me how hard it's been with Kaylee setting her up all the time with the pushy guys they meet. That's why she was ditching her drinks Saturday night, she didn't want to end up doing something she knew she'd regret."
"So then I assume she's done being a part of the terrible trio?"
"Yup, she laughed when she heard we called them that." Madison laughed herself and sounded so normal it made Hilly's heart rate slow. "She suggested we call Kaylee and Bailey Bi-Bitch now."
Hilly snorted, which made them both laugh even harder. "Oh my god, she'll fit right in. I can't wait to get to know her better."
"We'll see," Madison said after they calmed down. "It's early. We haven't even talked that much or kissed or anything."
"Well, let me know if I can do anything. I'll host a sleepover and watch movies downstairs by myself if you want. God knows you've covered for me and Ben enough this weekend that I owe you that much at least."
Maddy cleared her throat and chuckled. "That might be too… weird."
"Why?" Hilly wanted Madison to feel the same happiness she felt.
"I've… uh… had a crush on you for years."
"Trust me, if I ever swung that way, you'd be my girl, but it's just not me."
"I know, but making out with someone in your bed?" Madison made a shivery sound. "I just couldn't do it. I mean, when we slept there I got all moony before."
"Okay, but I mean it, I'll do anything you want me to. Hey, we can even double date after my birthday next month!"
"Oh, Hilly, I'm not ready to tell anyone else!"
"Don't worry, I didn't mean saying anything about you guys, but we could still all go out and do stuff together. Who would even notice with me and Ben making goo-goo eyes at each other."
"That's true. It would be good camouflage if nothing else. I need to call Ashley! I'm so glad you understand."
"Maddy, I love you. You're like the sister I never had."
"I love you, too, and I am glad for you and Ben. I can tell how strong you feel about him."
"He's amazing," Hilly sighed. "But between Mom and Shane asking about what's going on between us I'm ready to scream."
"Fill me in at school tomorrow!" Maddy was clearly too excited about talking to Ashley.
"I will! Goodnight."
Hilly shut her eyes and rolled her head back and forth against the wall with a smile of relief. She was still enjoying the peaceful moment when her door slammed open and Pete yelled, "Mom said to come set the table!" Then he was gone.
By an unknown, unspoken agreement, no one brought up Ben during dinner. Hilly eyed her father, Frank, with suspicion but he seemed oblivious to the undercurrent of tension she felt. Frank asked her questions about the trip, but instead of Ben he asked how the concerts went and what moves she used to bring down the big guy that had drugged Kaylee. She answered carefully without mentioning Ben too often, but each time she did Shane sighed audibly.
After dinner, she helped clean up because it was her week to do dishes. By the time she was finished and returned to her room to put on her nightshirt, her father was sitting on her bed. His thin smile was her only clue to what he wanted as he motioned for her to close the door. When she did and turned back around he was sitting with his hands in his lap.
"You're mom has been driving me crazy all afternoon," he said at last.
"She has?" Hilly's stomach clenched like she'd been gut punched.
"I bet you thought I'd be the one freakin' out when you've got your first boyfriend," he chuckled. "But I've been ready for this day for a long time now."
"You have?" she asked, feeling her head spinning as she sat beside him on the bed.
"I've told you what young guys can be like. I even taught you how to defend yourself." He reached over to touch her cheek. "Now I've got to trust that you're smart enough to know what you want and strong enough to make the right choices. Just remember how much I love you, baby."
Hilly felt her chest loosen as her tears fell. "Oh, Daddy."
He pulled her into a tight hug and kissed her hair. "Does Ben make you happy?"
"Yes," she whispered. "I know we're young—"
"Shh," he interrupted. "Enjoy it for as long as it lasts, but if he breaks your heart I'll break his neck."
"Thanks, Dad," Hilly said as they both chuckled. She pulled away to wipe her eyes.
"Your mom and I met in high school. We survived college, the NFL, and nearly losing everything right after you kids started coming when we started the business. Just promise me you'll be careful."
"I will," she promised herself as much as him.
"Good," he said and patted her leg before standing. "I'll take care of your mother." He looked around the room, his eyes pausing where her posters and stuffed animals had been. "Have you thought about what you want for your birthday next month?"
"Different furniture. Maybe some new clothes. I think I'm getting a little too old for the tomboy look."
He smiled down at her. "I'll match you dollar for dollar to get the furniture you want, but I'll let Mom handle the clothes. She's been wanting to go shopping with you for that girly stuff for years now."
"Thanks, Dad, but I don't have time for a job right now. School is kickin' my ass, especially algebra. Ben really is comin' over to tutor me."
"You can probably sell this furniture for a little bit. And talk to your sensei, Will, down at the dojo about splitting the take on you doing a women's personal safety course. When the news gets out about how you helped that girl, I bet you'll be able to fill in a class just from your school. He'd be a fool to pass on that kind of deal."
Hilly smiled and nodded. "Great idea!"
He smiled back as he opened the door. "Don't stay up all night talking to Ben."
"I love you, Daddy."
He shut the door as he left and Hilly fell back on the bed to grin at the ceiling. Her phone buzzed and she dug it out of her back pocket. Ben had sent a2 – b2.
She laughed and typed in (b – a) (a + b).
Are you sure you need me to tutor you?
She pressed his contact to make a call. When he answered she said, "I need so much more than a tutor right now."
"How'd it go tonight?" he laughed.
"Better than I expected, but not as good as I'd hoped."
"Can we talk?" he asked with a sensual hint in his voice.
"Let me lock the door so I can change into my nightshirt." She put the phone down to lock the door, pull back her sheets, and strip down to nothing. "Okay," she said as she slid naked on the cool sheets.
"My parents made a big deal about the age difference. Plus they knew I dated Kaylee for a while." Hilly heard the rustling of sheets. "I just stuck to our story and made out like I was grateful for you keeping Kaylee from doing something stupid after we broke up."
"Mom and Shane drove me crazy with questions, but Dad is actually cool about it. He said he trusts me to know what I want and to be safe about things. I'm kinda blown away right now." They were both silent for a moment, then Hilly added, "Oh, he also said if you break my heart he's gonna break your neck."
Ben laughed in her ear. "Why would he have to? You could do it yourself!" he said.
"I miss you already," she whispered as her left hand squeezed her breasts. The little zing it gave went straight to her warming center. "How's that hand lotion?"
"Cold and not nearly as interesting as the slippery stuff you make." He took a deep, noisy breath. "I can still smell you on my fingers."
The thought of how he got her scent on his fingers made her flood. "Oh, Ben."
"What are you doing right now?" he asked.
"Touching myself," she gasped as her fingers spread her lips to feel her slick center. "And I'm so slippery."
"God, I'm so hard it's vibrating."
She could hear his breathing deepen as she rolled over on her stomach. "I'm face down and lifting my ass up for you." Her fingers continued to reach back as she tilted her hips to bring her opening within easy reach. It stung when she put her middle two fingers in deep, but it felt too good to stop.
"I wish I was there," he moaned. "I'd fill you up like that last time at the hotel."
"That was the best for me." The memory of being filled with him made sparks shoot along to prickle her skin. "You felt so good, so hot." When her fingers reached as deep as she could make them go, it still wasn't deep enough.
"No, you were h-hot inside," he stuttered. "Oh God, Hilly!"
"Cum for me," she whispered. "I'm so close right now, but I need to hear you."
"So close," he whispered. "Go with me if you can."
The image of him stroking himself while she did the same pushed her over the edge. "Ben," she gasped. "Now!"
His straining grunt was all she heard while her body shook and twitched. She kept rubbing her swollen nub as her orgasm continued to build. Listening to him start to breath again told her he was slowing down, but she was still quaking. Her tense whine announced her own completion as she collapsed on the bed with her hand cupping her wet mons.
"I made a mess," Ben chuckled. "It's all over my chest and stomach."
"Taste it," Hilly dared. "Describe what it tastes like to me."
Ben was silent for a moment and she couldn't tell if he was actually doing it.
"Kinda salty and bitter, but not that bad." He sounded surprised.
"You've never tasted yourself before?"
"Only on your lips this weekend. Have you?"
"All the time," she said as she pulled her hand to her lips. "It makes me feel dirty in a good way." Then she licked her fingers with a low hum.
"I love the way you taste," he said. "I could eat you up and never get enough."
"Maybe we can try that someday," Hilly teased as she rolled over. "Oh, that was so good."
"When I see you tomorrow in choir, I'll brush my lips with my fingers so you'll know what I'm thinking about."
"I can't wait to see you again," she whispered as she felt her body relax in a post-orgasmic glow.
"Go to sleep and time will go faster." His voice had the same sleepy contentment as her own.
"Goodnight," she whispered.
"Goodnight and sweet dreams."
And they were.
Source: reddit.com/r/sexystories/comments/3a0z2x/hilly_and_ben_their_first_date_1_mfmast
It’s nice to see more about these two. Thanks for sharing!