Brooke's First Time

Thanks to lovecraft68. We worked together on a story for the Odd Couplings Challenge, but I couldn’t see it through. This story features the character JD from By Demons Driven, a collaboration between lovecraft68 and xelliebabex. You can find their story here: It’s pretty damn good.

Both participants in this story are over eighteen.


Her virginity goes to her bad-boy friend.

Brooke peeked out of the curtains in the living room until her aunt’s car disappeared around the corner. She went to the door of her childhood bedroom and fingered the letters on the door, spelling out her name. As she put her hand on the doorknob of her room, she felt a nervous shiver run through her body. JD, the boy she’d loved since high school, was in her room. Waiting for her.

She thought about all the times she’d practiced kissing her pillow. JD had kissed her a couple of times, but just soft, little, friend-type kisses. She wanted to be kissed like one of his slutty girls. She wanted to feel his tongue in her mouth and his hands on…

She shook her head and tried to pull herself together. After a deep breath, she opened the door and saw JD sound asleep on her bed in the dim light of her bedside lamp. His head was on her pillow, and his arms were wrapped around the purple afghan her grandmother had crocheted when she was eight. She had to stifle the aww that tried to escape her lips.

He was adorable. His hair was messy, and he had the first trace of stubble from his morning shave. His face was soft and innocent and sweet, the exact opposite of how he usually looked—tough, angry, and sneering at the world.

Brooke felt the overwhelming urge to kiss him, but she chickened out. Instead she sat down on the bed and pushed a stray, jet-black lock off his face. Her touch woke him, and he smiled when he opened his eyes.

“Mmm…I dozed off there,” he said.

“Yeah. You drooled on my pillow, you big oaf.” She smiled and pushed another piece of hair out of his eyes.

He pushed himself up so that he was sitting, leaning back against Brooke’s headboard. “I’m sorry. I haven’t been sleeping too good, I guess. Your bed is really comfy.”

“Were you sleeping the whole time?”

“Nah. I snooped a little bit too.” His grin was devilish.

“Hey!” she said as her fist struck out playfully against his ribs. “You didn’t read my diary, did you?” She scrunched up her nose, letting the snooping comment pass. She giggled softly and said, “This is weird.”


“This. You. Here. In my room. I mean, I know you have gotten comfy in a lot of girls’ beds, but I didn’t expect to see you in mine,” she said.

“Technically I’m on it, not in it.” He grinned again, ignoring the comment about being in other girls’ beds.

Brooke licked her lips nervously. JD moved closer to her, as if on autopilot. Brooke took a deep breath, trying to relax. His mouth opened a bit, and his eyes dropped to her lips. She closed her eyes and hoped.

When his lips touched hers, she felt a spasm shoot through her stomach. She tried to relax and follow his lead. His lips lingered on hers for a moment before she felt his tongue brush against her top lip. She melted into his body with a barely audible moan. His lips slid across hers, and he was rewarded with a whimper that made his heart pound in his chest and his cock stir.

She put her hand on his cheek, feeling the stubble against the silky skin of her palm. He leaned into her hand enjoying the gentleness of her touch. JD didn’t have too much in his life that was gentle.

He nuzzled his chin against her palm, making her smile. He smiled back, his eyes crinkling. That smile, the soft, almost shy smile, made Brooke’s heart sing. His usual smile was the smirk that he gave everybody else. This was her smile, and she loved it.

He relaxed back onto the pillows against the headboard, backing off just enough to make Brooke come to him. She leaned in and pressed her lips into his, her hands coming to rest on his chest. JD forced himself to be patient, to let her set the pace. Her lips parted, and he struggled to keep from thrusting his tongue into her mouth. He teased her bottom lip with his tongue, inviting her to do the same.

She probed his mouth tentatively, wondering if she was doing it right. She could feel his heart racing against her palms, and she hoped that was a good sign. His hands reached for the base of her jaw and slid around to the back of her neck, just like she had seen him do to one of his slutty girls. She felt a rush of heat through her body, and she moaned again, making JD’s cock swell against her.

She pushed herself up against his chest, rose to her knees, and looked down at JD. Her hair was up in a plastic clip, like she always wore it. JD moved his hand to the clip and released it. As her hair spilled down around her face, he pulled her to him and kissed her again. This time he didn’t fight the urge. His tongue pushed its way into her mouth, meeting hers.

After a moment, JD ran his fingers through her soft, brown hair, and broke the kiss. “You should wear your hair down more often,” he said in a husky voice. “You’re prettier with your hair down. I mean, you’re pretty with it up but…”

Brooke took a shaky breath. She didn’t know she was pretty.

JD’s arms wrapped around Brooke’s waist, and he pulled her close, taking advantage of her shakiness. His hand returned to her hair, and he pulled it, just hard enough to tilt her head back. She gasped, but didn’t pull away. He lowered his head and touched his lips to the soft, creamy skin of her exposed neck.

“That tickles,” she whispered.

He worked his lips slowly along the length of her neck. He reached her ear and gave it a flick with his tongue. He moved his head toward the other side of her neck, but Brooke stopped him by pressing her lips hard into his. He slid his hands between them and pulled up his shirt. He broke the kiss long enough to pull his shirt up and toss it aside.

“JD…What…what are you doing?” she asked as her eyes roamed up and down his bare chest.

“Getting closer,” he mumbled before pressing his mouth over hers, harder this time. He hoped she wouldn’t realize that he’d read in her diary that she wanted to feel him so close, even the thin layers of cotton weren’t there to separate them.

“Oh,” she moaned softly. Her hands ran down his naked skin. She brushed her fingertips over his nipples, making him shiver.

“Tickles,” he said into her mouth.

He moved his hands to her thighs, on top of her denim skirt. The skirt fell just above her knees when she was standing, but it had ridden up leaving a lot of bare leg showing. He moved his hands down to her knees, and when he slid them up, he slipped them under her skirt.

Brooke broke the kiss this time. “JD…I…I’ve never…”

“Shh,” he said. “We won’t do anything that makes you uncomfortable. Just relax. If you want to stop, we’ll stop.”

“OK…I…OK,” she said, relaxing her body. JD pushed her gently and rolled her onto her back. He ignored the look of panic that crossed her face, leaned over her, and kissed her on the nose.

“Trust me,” he said with his sweet smile. He put his hand on the side of her face and kissed her again, distracting her a bit. Her eyes were closed, and her body was relaxed. As his tongue probed her mouth, his hand slid down from her cheek to her neck to her arm. He slipped his hand to her waist and let it rest there for a moment.

Before Brooke could register what was happening, JD slid his hand slowly up her side. Her breath quickened as he approached her breast. He kissed her harder to keep her from speaking, afraid that she would stop him.

He had felt up a lot of girls in the last few months, but he had never felt this kind of anticipation as his hand was poised to make contact with a breast. This was Brooke, for Christ’s sake. His cock throbbed and his breath was ragged. He decided to go for it, and he cupped her tit over her shirt.

Brooke gasped and her eyes snapped open. “JD?” she said.

“It’s OK,” JD said. “I got you.”

“Go slow,” she said. “I’ve never done this before.”

“I know. Just trust me.”

He moved his hand, just a bit, feeling the firm flesh beneath. Brooke took deep breath after deep breath, her head swimming with desire and confusion.

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JD moved his hand to the other breast and gave it a gentle squeeze. Brooke’s sigh spurred him on, and his fingers moved to the buttons on her blouse. He did not wait for permission before unbuttoning the first three buttons.

He lowered his head and placed gentle kisses on her neck and chest while he continued to work on the buttons. When the last button slipped through its hole, JD ran his hand up to her shoulder and slid her shirt over her shoulder. He gazed down at her body, taking in her simple, white bra and cream-colored skin. Her chest heaved as she panted. Her eyes were closed, but she made no attempt to stop him.

JD traced the outline of her bra with his tongue before slipping the straps down her arms. Just before the fabric slipped from her breast, JD paused. “Is this OK, Brooke?” he asked gently. She opened her eyes and nodded, her heart pounding in her chest. “Good. I want to see you,” he said, kissing her on the nose and pulling the cups down over the soft mounds. His breath caught in his throat when he spied the rosy nipples hiding beneath. “You’re so beautiful,” he rasped. “Can I take your bra off?”

She nodded, and sat up. She fought the urge to cover her naked breasts as he removed her shirt and her bra. He wrapped his arms around her, pressing his naked chest against hers. He could feel her erect nipples against his smooth skin. He rubbed her back and kissed her again.

“JD,” she started, “I can’t believe you’re here. I can’t believe we’re doing this. I mean, I don’t even know what I’m doing.”

“You’re doing great, sweetheart,” JD mumbled while he kissed her again.

He laid her back on the pillow and got to his knees on the bed next to her. He bent his head over her breasts and took her nipple into her mouth. He circled the hard nub with his tongue, and then scraped it gently with his teeth. She shivered hard enough to pull her nipple out of his mouth.

“Did I hurt you?” he asked. She shook her head and arched her back, silently asking for more.

JD took the other nipple between his lips and sucked gently, his tongue probing the flesh. While she moaned from the attention on her nipple, his hand went to her thigh. He moved his hand up under her skirt until his fingers brushed the cotton of her panties. He guessed that they were white.

He ignored her gasp and pushed ahead, placing his hand over the front of her panties. His fingers rubbed in slow circles. He could feel her pubic hair through the fabric.

Brooke’s head was screaming. She knew she should stop him, but she wanted him. She wanted to know how it felt to be touched in places she rarely touched herself. She was throbbing under his hand, and she suddenly understood that she would let him do whatever he wanted to her body. She loved him, and this would be her gift to him. And to herself.

His fingers slipped in through the side of her panties. She sucked in a sharp breath and nodded. “Are you sure?” he asked. She nodded again and tried to relax as his hands wandered under her clothes. He ran his finger over her slit, feeling her juices soaking through the fabric.

“You’re so wet, sweetheart,” he whispered.

She blushed, not really understanding why that happened. “I’m sorry,” she whispered.

“No, no,” he said. “Wet is good. Wet means you like it. Guys get hard; girls get wet.”

“Oh,” she said, embarrassed that she didn’t know something so simple. “Are you…hard?”

“Very hard. Hang on. I’ll show you.”

He stood up and slid his jeans over his hips, leaving on his white briefs. Brooke stared at him with her eyes as large as saucers. She could see the bulge through the fabric, but didn’t have any idea what it would look like if he wasn’t hard.

JD took Brooke’s hand and pressed it to his erection, moaning as she squeezed gently. “Did that hurt?” she asked, alarmed.

“Nooo,” he groaned. “Oh, Brooke.” Still standing beside her, he pulled her skirt up so that he could see her panties. He was wrong. They were pink.

“Can I pull down your panties?” he asked. Brooke could hear the hope in his voice. She swallowed hard and nodded. He reached up, under her skirt with both hands and gave the cotton a tug. She lifted her hips to allow him to take them off. He tossed them aside, like he had his shirt.

He smiled at the sight of her full pubic hair. Most of his slutty girls were trimmed or shaven. He loved knowing that this wasn’t planned. Brooke wasn’t waiting for a day on the calendar to be added to his list of conquests.

“Let me get this skirt out of the way, then I’ll take my underwear off too, OK?” he said. He was trying so hard not to rush her, but he couldn’t hold on much longer.

“OK,” she whispered. She was nervous. This was too many firsts all at once, but she wasn’t sure she could stop this. She didn’t want to disappoint JD, and she wanted it. She wanted him. She shivered, partly from desire, partly because her virgin skin was exposed to the chilly air and JD’s eyes.

He saw her shiver. “Here,” he said, covering her with the purple afghan. She relaxed a bit now that she was covered. She watched him pull his briefs down over his hips, and she jumped when his cock sprang free. It was huge.

“Oh my god, JD. I’ve never seen…” she said.

“It’s OK, sweetheart. I’ll be gentle with you.”

“I’ve only seen pictures in encyclopedias and biology books. I didn’t know they could look like that,” she said in a trembling voice.

“Brooke,” he said as he climbed back onto the bed and joined her under the afghan. “Do you think maybe you could touch it?”

She nodded. JD took her hand and wrapped it around his shaft. He left her hand there for a moment and let her explore, but she was too nervous to move. He put his hand over hers and moved it up and down his length.

“Just like that,” he said.

He took his hand away and let her continue. She got a little bolder and gripped him a little tighter. He moaned, knowing he wouldn’t be able to take much more if he wanted to go further. He reached for her again and caressed her breasts while she stroked.

“I’m gonna touch you down there now, OK?”

“OK,” she whispered.

He pushed his hand down her flat stomach until his fingers reached her bushy hair. He paused to make sure he wasn’t rushing her, but he couldn’t hold back. He slid his finger into her slit and made a noise at the back of his throat when he felt the wetness pooled there.

“Oh my god, Brooke. You are dripping wet. I’m so happy this is turning you on,” he said. He explored her pussy with his fingers, reveling in the soft sounds that came from her when he touched the right spots. “I think you’ll really like this part. Just relax.”

He put two fingers over her clit and swirled in counter-clockwise circles. Brooke released a loud “oh,” encouraging him. After a moment, he moved his fingers to her opening. “Is this OK?” Her deep breath was enough of an answer. JD swirled his finger down until he reached her opening. He let it rest there then swirled just a bit through her wetness.

“I’m nervous, JD,” she said, her voice trembling.

“Shh. I’m gonna be so gentle with you. Just relax.” He removed his hand and brought his finger to his mouth.

“Did you just…?”

“Yes. I did. You taste so good, Brooke. Can I put my mouth down there?”

Brooke shook her head, just a little bit. “No, please don’t do that, JD. That’s gross.”

“OK. I won’t…But it’s not gross, you know.”

Brooke’s body tensed when she realized that JD probably expected her mouth “down there” too.

“What’s wrong?” he asked as his fingers resumed rubbing her clit.

“Ooh,” she moaned before she could answer. “Oh. That feels good.”

“Good. Keep telling me when I do something you like, so then I can keep doing it. But relax. Why are you so tense?”


“Brooke, you can tell me. What are you afraid of?”

She took a deep breath just as he increased the pressure on her clit. Her head fell back against the pillow, and she rushed to get the words out before she changed her mind. “I know that you want to put it in my mouth, but I’m just not ready for that.”

JD laughed out loud at the terror on her face. “Oh, Brooke. No. I wouldn’t ask you to do that. Not tonight. I just want to be here, holding you and making you feel good,” he said. “We don’t have to do anything you don’t want to do.” That kind of reassurance always got him what he wanted.

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He paused and gave her a devilish grin. “But you do want me to keep touching you there, don’t you?”

Brooke smiled and nodded.

JD stopped talking and moved her knees farther apart. His eyes roamed up and down her naked body, and Brooke swore that she could feel his gaze on her skin. He ran his palms over her hard nipples one more time before replacing his hand between her thighs. This time he poked gently at the folds of her pussy, probing for the right spot. When he found it, he pressed, hoping to feel her flesh yielding for him.

Brooke winced at the pressure, but nodded to let JD know it was OK to go on. He knew that it would be more painful for if he prolonged it, so he tried a new tactic. Just as he pressed into her even harder, he tweaked her nipple with his other hand.

“Ouch!” she yelped. “Why did you pinch me?”

“So you wouldn’t feel my finger popping inside you,” he said, leaning down to kiss her again.

“Oh my god. Your finger is inside of me?” They kissed while he slid his slippery finger in and out of her. They continued kissing when he added a second finger. Brooke jumped at the pressure, but after a few moments, she had made her decision.

“JD?” she asked, breaking the kiss.


“Do you… Do you have a…?”

“Do I have a condom? Is that what you’re asking me?” he said.

“Yes. I think I’m ready,” she said, her voice a whisper.

“Are you sure?”

“Get it before I change my mind!” she said. “Don’t let me chicken out.”

JD got the condom out of the pocket in his jeans and tore open the package. “You do it,” he said with a smile.

“I don’t know how!” Brooke said.

“Yes you do. We were in the same health class in tenth grade. Remember the day with the bananas?” Brooke rolled her eyes. “Here. You just put it here. Yeah, like that. Now you push it down with your hand, and I get a little bonus hand-job.” His smile widened, and Brooke couldn’t help but smile back. She did just as instructed, hoping she was doing it right. When the condom was in place, JD kissed her nipples and laid her back on the bed.

“Tell me if I’m hurting you, and I’ll stop, OK?”

Brooke nodded and spread her legs apart. JD knelt between them, and lowered himself over her body. He looked into her eyes, kissed her, and gave her one more opportunity to change her mind.

“Are you sure?”

“Do it. I’m ready.”

JD took his cock in his hand and lined it against her opening. He applied a little bit of pressure, causing Brooke to tense up and yelp in pain. He released the pressure and played with her nipples.

“Try again,” Brooke said after a moment.

After several unsuccessful attempts to penetrate her, JD said, “Here. I’m gonna try something different.”

Brooke closed her eyes and tried to relax.

He spread her lips apart with his left hand, and guided his cock with his right. He placed it between her lips and began to pump it along her pussy, rubbing from her opening up to her clit. Back and forth he rubbed, slowly at first, but picking up speed when Brooke began to moan and move her hips to meet him.

“Do you like that?” he whispered.

“Mm hmm,” she moaned.
He moved his hand to her nipple, and rolled it gently between his thumb and forefinger. When she moaned again, he bent to kiss her. He hoped that his tongue probing her mouth created the distraction he needed, and he slipped his right hand back to his cock. His fingers pinched lightly at her nipple, causing her to suck in a deep breath, and JD took his opportunity.

As he squeezed her nipple again, he bit her lower lip gently, lined the head of his cock against her wet hole, and plunged inside of her, meeting with resistance that reminded him that she was a virgin. A shudder raced through his body at the thought of taking Brooke’s virginity after all this time.

Brooke’s hips tried to move away from the intruder as she cried out in pain, but JD held on tight and thrust into her again even harder. This time he felt her warm wetness even farther down his cock, and he knew he was close to breaching the barrier that was keeping him from entering her all the way.

“Oh, JD. It hurts. Go easy,” Brooke said in a shaky voice. Her eyes opened and tears spilled down her cheeks.

“Do you want me to stop?” JD said, hoping silently that she would say no. He wasn’t sure he could stop if he tried.

“No. Just do it. Fast,” she said, panting a little.

“OK. Take a deep breath.”

As she inhaled, he thrust his hips as hard as he dared. This time he felt the resistance on the head of his cock give way, and his pelvis slammed between her legs. Brooke cried incoherently as the pain shot through her body, but when JD started to pull out, she put her hands around her waist to stop him.

“No,” she said. “Just give me a minute to adjust.”

JD groaned and kissed her lips. “Good girl, Brooke. You are so warm. And so tight.”

“Holy cow,” she said. “I can’t believe this is happening.”

“Are you happy?” he said.

“Yes. Really happy,” she said. Fresh tears started to flow, and she said, “I’m not a virgin anymore, am I?”

“No, you’re not, sweetheart. Are you ready? It’s not gonna take me long.”

Brooke nodded, and JD pulled out almost all the way. He pushed his cock inside, slowly and gently, moaning all the time.

“Your pussy is so tight,” he whispered, reversing direction again.

“You can go a little faster, I think,” Brooke said.

JD increased the pace, but kept his movements smooth and gentle. He could see the pain reflected in her face, but he knew that he would keep going until he came. “I’m almost there,” he said. “Are you OK?”

“Yes. Keep going.”

“Oh my god. I’m gonna come. Oh god, Brooke. I’m coming.”

He slammed all the way into her, much harder than he meant to, and cried out, much louder than he meant to. Brooke wrapped her arms around him and held him tightly to her. She was crying from pain and joy and love all at the same time, and when he pulled out of her and collapsed on top of her, she smiled through her tears.

JD kissed her one more time, slipped the condom off into a tissue, and fell asleep on her pillow.

Brooke went into the bathroom to clean up, and she examined her face in the mirror, trying to see if she looked any different now that she wasn’t a virgin anymore.

“Nope. Just the same, mousy me,” she said to her reflection. She didn’t know what she expected, but somehow she thought she’d look older or wiser or something.

After her shower, she slipped on her terrycloth robe and went to her room to ask JD if he wanted her to heat up some lasagna for him. Once again, his sleeping form made her heart melt, and she decided not to wake him.

She climbed up onto the bed and slipped under the covers, trying not to disturb JD. He looked so peaceful and so relaxed, lying on his side with his arm over the heart-shaped pillow she’d kept on her bed since childhood. Before she turned off the bedside lamp, so took a moment to look over his body. His cock had softened, and no longer looked like the battering ram that had broken her hymen. She leaned over him and pulled the purple afghan over his naked body. She kissed him on the temple and on the cheek as she tucked him in.

“I love you, JD,” she whispered as she turned off the lamp. With her back to him, she didn’t see the smile cross his face.

Updated: December 20, 2016 — 7:00 PM

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