Pumpkin
Copyright© 2024 by DeepInside
Chapter 4
Coming of Age Sex Story: Chapter 4 - Penelope's eighteen-year-old pumpkin sized breasts make her a target in school. Disclaimer: All characters in this story are 18 years of age or older. All students portrayed in a school setting or otherwise are high school seniors that are about to graduate and are all 18 years of age.
Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft mt/Fa Mult Teenagers Blackmail Coercion Consensual NonConsensual Reluctant Romantic Heterosexual Fiction School Anal Sex Analingus Cream Pie First Facial Oral Sex Safe Sex Tit-Fucking Big Breasts
“What the hell!” Brad said as he drove away. “I must be losing my mind! Did that really happen?”
He couldn’t shake the sight of Pumpkin’s mom’s mouth sucking his cock. It was like a scene from a porno, but it happened. He looked in the rearview mirror and saw Penelope’s house shrink into the distance. The image of her mother’s lust as he fingered her to an orgasm burned into his brain. He didn’t know what to feel.
The rifle hanging on a rack in the den was a stark reminder of what could happen if Pumpkin’s dad found out. He drove in a daze, his thoughts jumbled.
His phone rang. Pumpkin was calling. “Hi,” she said. “Mom and I had a talk. She’s not going to tell Dad. She said she likes you. What did you say to my mom, she has a big smile on her face?”
Brad went pale. “Um,” he stuttered. He didn’t know how to explain what happened. “We ... have an agreement.”
Penelope sighed. “I know, Mom told me she would need to have some private time with you, to make sure you were treating me right,” she said. “I was so scared I would lose you.”
A new fear raced in Brad’s mind. “Um, what did your mom say?”
“Well, she said she won’t tell Dad, but we need to be more careful,” Penelope replied, sounding both relieved and excited. “We can fool around in my room, but we can’t get naked or fuck. But listen to this! I can continue to give you oral sex! Can you believe that! And here I thought my mom was a prude!”
Brad’s grip tightened on the steering wheel. “What else, Pumpkin? Did she say anything about me?”
“No,” Penelope’s voice was innocent, “but she said that if we’re going to go all the way, we should do it right and use protection. She’s going to take me to the doctor so I can go on birth control pills. Oh, and she said she’s okay with us doing other things in the meantime, like anal sex.”
Brad’s mind reeled. This was not what he expected from a parental chat. “Anal?” he echoed. “Your mom gave me permission to fuck your ass?”
Penelope giggled. “Well, she didn’t say it like that, but yeah, she’s cool with it as long as we’re safe and use condoms.”
Brad couldn’t believe it. “Your mom is amazing,” he murmured, still in disbelief. “I’m going to stop at the drugstore on the way home.”
“Good idea,” Penelope enthused, “Can go to your house after school tomorrow?”
Brad nodded, his mind racing with the implications of this strange relationship. “Yeah, that sounds perfect,” he said, “my parents don’t get home for hours.” His phone pinged. Penelope sent him a picture of her huge bare tits. “Pumpkin, you’re going to get us both in trouble,” he said, smiling despite himself.
“I feel bad now for making you delete all those photos you took in the girl’s bathroom. Now you have a personal one from me to you! Will you send me one of your cock later?”
Brad nodded, his cock twitching at the image of Pumpkin’s naked tits. “Definitely.”
That night, Brad couldn’t shake the uneasy feeling that his encounter with Pumpkin’s mom would be his downfall. Her mouth had been so demanding, so welcoming She took control of the situation, blackmailing him in exchange for keeping her silence. It was a deal he loved and hated, but what choice did he have? He wanted to be with Pumpkin more than anything, and if this was the price to pay, so be it.
He was jacking off looking at Pumpkin’s tits and thinking about her mom’s mouth. The juxtaposition of the sweet and the forbidden was a heady cocktail. His thoughts were interrupted by a knock on his door. “Brad, can I come in?” It was his mom. He quickly stuffed his phone under his pillow and covered himself up. “Yeah, come in.”
His mom peeked around the door. “I wanted to check on you, sweetie,” she said, her voice concerned. “You were quiet at the dinner table. Are you okay?” She walked in stopping at the foot of his bed.
Brad nodded, trying to keep his face neutral. He almost told her about Pumpkin but changed his mind. “I’m good, Mom,” he said, hoping she wouldn’t notice the tent under the covers. “I have a lot on my mind.”
“Well, if you need to talk, I’m here,” she said, her eyes searching his face. “You know you can tell me anything.”
Brad nodded. “Thanks, Mom. I appreciate that,” he replied, “I love you,” his voice sincere.
“I love you too,” she said, her eyes shifted to the large hard lump under the light sheet and she let out a gasp. Her son had a huge erection. She felt her face go red in embarrassment but couldn’t look away. He had to be twice the size of his dad. “Um, good night, honey,” she mumbled racing for the door. I hope he didn’t notice me staring! she prayed.
Brad smacked himself in the head. “Fuck! Could this day get any crazier? My mom couldn’t take her eyes off my hard cock!” At the same time, a text came in from Pumpkin. “hey, where’s my dick pic?”
Brad rolled his eyes, Pumpkin lost her shyness. He stroked himself to full length and took a quick photo then hit send. His phone beeped immediately. “Thanks babe, I needed that. My fingers are busy!: ) Can’t wait for tomorrow to come. Get it? Come!” He couldn’t help but laugh at her corny joke.
He pulled a tissue out of the box on his night stand. He jerked himself off thinking of Pumpkin, her mom and when he exploded it was to the image of his mom’s shocked face.
The next day school dragged by like a snail going uphill. Everyone in school was surprised by his new relationship with Pumpkin. Chad refused to talk to him, Brad knew he’d lost his wingman, but maybe time would heal their rift.
The anticipation of repeating yesterday’s experience with Pumpkin was almost too much for Brad to handle. His mind was a whirlwind of thoughts: her mom, the things they did in the den, and what he’d agreed to keep doing. And then there was the long hug his mom gave him this morning. It was all so confusing.
At lunch, Brad and Penelope sat together, holding hands under the table. They talked in hushed tones about their plans for after school. He pulled a condom out of his back pocket and showed it to her. She grinned and squeezed his hand, her cheeks flushing a beautiful shade of pink.
“Are you ready to take this to the next level?” Brad asked. “Or we can wait.”
Penelope nodded eagerly. “I’m ready,” she whispered back. “I’m so ready, I’m soaked!” she giggled. “Mom said I have to tell her all the details of what we do, especially when we “do it”.
Brad’s heart skipped a beat. This was getting more bizarre by the minute. “Your mom wants details? About when we have sex?”
She nodded. “That’s the deal I made with her to keep our secret from my Dad. She’s so cool! I can’t believe she wants to help me?” Penelope enthused, “Don’t you love my mom?”
Brad didn’t know how to feel about it, but he nodded. “Yeah,” he replied. “Your mom’s pretty ... amazing.” He was still in shock over the whole situation. The bell rang, signaling the end of lunch. “I’ll see you after school, Pumpkin,” he said, kissing her goodbye.
His classes were a blur, his mind racing with the thought of what awaited him after school. “Would Pumpkin tell her mom everything they did? Would he have to do more with her mom?” The thought made Brad’s cock twitch in his pants. For the first time, he pictured himself fucking Pumpkin’s mom. She was beautiful, with her blonde hair and green eyes. But she was his girlfriend’s mother. He felt conflicted but also incredibly aroused by the idea.
After the final bell, Brad and Penelope sprinted to his car. They kissed and he opened the door for her. On the way to his house, Pumpkin talked non-stop describing in explicit detail how she wanted to lose her virginity.
“I want to be looking into your eyes,” Penelope giggled, resting her hand on his thigh. “I want you to go slow and make it special. Do you think it will hurt? My mom said it would, but then it would feel good. She said to tell you to go down on me first and get me excited. Will you? Please?”
Brad swallowed hard. He had never felt so much pressure to perform for two different women at the same time. “Of course,” he assured her, “I’ll do whatever it takes to make it perfect for you, Pumpkin.”
“Mom also said,” Penelope’s voice went soft and shy, “that you should fuck me in the ass first. Then after I suck you hard, you will stay hard longer to make sure I have an orgasm. My mom sure does know a lot about sex! Don’t you think?”
Brad’s eyes widened and his hand gripped the steering wheel tighter. “I ... uh ... yeah,” he stuttered. “She looks innocent, but she’s not.”
Penelope nodded, her eyes sparkling with excitement. “I know!” she giggled. “She’s the best mom in the world. She wants me to experience everything!.”
They arrived at his house, and Brad felt his stomach churn. He was nervous about having sex with Pumpkin for the first time. Especially knowing her mom would hear all the details later. He parked in the driveway and turned off the engine. Fumbling with the house key he couldn’t get the door open. Penelope reached out and steadied his shaking hand.
“It’s okay,” she whispered, kissing him softly. “We can take our time.” She never thought Brad would be nervous. He was the cool kid with the classic car, the one who could get any girl he wanted. But here he was, stumbling over his words. It was kind of cute.
They went inside, and Brad led her to his room. They both knew the drill; they had been here yesterday. But this time it was different. This time they were going all the way. Pumpkin was the first to get undressed. Her clothes dropped to the floor revealing her curvy body. Brad’s eyes drank her in. “You’re perfect,” he said. She looked like a goddess standing there in her white lacy bra and panties.
Penelope blushed and stepped closer to him. “Take my bra off,” she whispered, her eyes locked on his. Brad’s trembling hands reached around her back and unhooked her bra. Her tits bounced free, and Brad couldn’t help but stare in awe. They were beautiful, big, round, and she was all his. He kissed her softly, taking his time to savor the moment. His hands slid down to her ass and squeezed it gently. “My mom said for you to use your teeth to take my panties off. Will you?”
Brad let out a groan. Her words sent a bolt of excitement through him. He knelt before her, his hands resting on her thighs. He kissed her stomach and moved lower, his teeth grazing the waistband of her panties. He bit them and shook his head trying to get them down. He felt the heat from her pussy. It took several minutes, but Pumpkin stepped out of them, leaving her bare before him. He took in her beauty, her neatly trimmed bush and plump pussy lips. “You’re so beautiful, Pumpkin,” he whispered leaving a trail of kisses.
Pumpkin opened her legs and offered herself to him. Brad kissed the edges of her pussy, teasing her. She squirmed, her hands in his hair as she guided him closer to the spot she wanted most. He licked her clit and she moaned, her body jerking as he sucked on it gently. “Oh, god, Brad! That feels amazing!”
He didn’t know if it was the pressure of her mom’s expectations or the excitement of finally being with Pumpkin, but Brad felt like he was going to burst. He stood up and kissed her, letting her taste her sweetness. “Are you sure you’re ready for this?” he asked. His eyes held hers, searching for any sign of doubt.
She smiled and undid the buttons on his shirt, pulling it off his wide shoulders. “Yes, Brad, I’m sure,” she whispered. She dropped to her knees and undid the belt on his pants and then the zipper. His pants and boxers came down together and he stepped out of them. He was as naked as her. Her eyes focused on his cock bobbing in the air. “Looks like you’re ready too,” she laughed, stroking it lightly. “Do you want to come in my mouth first?” She paused. “Or, we can do anal? My mom gave me some lube.”
The words ‘anal’ and ‘lube’ hit Brad like a ton of bricks. He had never done anal before, but the idea of fucking Pumpkin’s tight ass was too tempting to resist. “Remind me to thank your mother the next time I see her,” he laughed.
“Oh! Wait!” Pumpkin exclaimed. “I promised to call her before we “do it””
She leaned down and for her discarded jeans. “Mom, it’s me. We’re in Brad’s bedroom. Yes, I told him he could do my bum first. Um, I don’t know. What, okay,” she handed the phone to Brad. “Mom wants to talk to you.”
Brad felt his cock twitch. “Um, hi, Mrs. Westbrook,” he said, trying to sound casual.
“Hi, Brad,” Mae’s voice was cool and collected. “Did you dream of me last night?”
Brad’s face flushed hot. “Uh, I had ... some thoughts,” he stuttered.
Mae’s voice grew sultry. “I know you did,” she purred. “Penelope showed me the picture you sent her. If you want to keep seeing her, you need to keep me happy too. Never forget that.”
Brad went silent. “Um, okay,” he said.
“Brad, Put the phone on speaker.
Brad complied. He looked into Pumpkin’s eyes. “Okay, Mrs. Westbrook,” he said, his voice shaking slightly. “Pumpkin can hear you too.”
“Pumpkin? Why do you call Penelope, Pumpkin?” Mae asked.
“It’s my nickname,” Brad replied, “because she has such big ... uh ... breasts.”
“Pumpkin, can you hear me?”
“Yes, mommy.”
“I want Brad to fuck your ass as hard as he can. I want him to make you scream and cry. This is your punishment for sucking Brad’s cock in my house without my permission! Brad, I don’t want you to stop until you come in her plump ass. And then I want you to send me a picture of your cum leaking out. One more thing, Pumpkin. I will be checking when you get home to make sure you’re no longer a virgin. Have fun kids!” she taunted. The phone went dead.
Mae’s voice echoed through Brad’s mind, sending chills down his spine. Pumpkin’s eyes were wide. He looked at her with concern. “Is this what you want? For your mom to know all this? To send her photos?”
Penelope nodded, her voice barely a whisper. “We have to. Or else Mom will tell Dad what we did. Dad might kill you in rage. He still thinks of me as his little Princess.”
Brad took a deep breath. He didn’t know how to feel about this, but he didn’t want to lose Pumpkin. He looked at her, kneeling before him, so eager and innocent. He felt his resolve crumble. “Okay,” he said, laying her phone on the bed. “Get me hard.”
Pumpkin nodded and took his cock in her mouth and started sucking with enthusiasm. Brad watched in awe. She was good, a natural, like her mother. He had to admit, having a mother and daughter sucking his cock was every teen boy’s fantasy come true, even if the situation was fucked up. Mrs. Westbrook was blackmailing them both. He tried to push those thoughts aside and focus on the moment.
Pumpkin took him to the edge and then stopped. She looked up at him with those big doe eyes. “Ready?” she asked. “I’m so nervous. Will it hurt?”
Brad nodded, his cock standing tall. “Probably, but I’ll go slow,” he assured her. Pumpkin got on the bed, breasts down. “Maybe get on your hands and knees and pull your cheeks apart,” Brad said. “I need to put some lube in your ... bum hole.”
He took the tube of lube from the bedside table and squirted it on her star. His slippery finger pushed the cold gel inside her. “Oh! It feels weird,” she whispered. “Can you use your fingers to let me get used to the feeling?”
Brad nodded, sliding his finger deeper. She winced at first but then her body started to relax. He moved his finger in and out, adding more lube. “Does that hurt?”
“No,” she whispered, “at least not too bad.” She pushed back against his hand, taking more of his finger. He watched as her tight ass swallowed his digit. It was an incredible sight. “Add a second finger.”
He complied, and she gasped. “Mom was right, it hurts, but I’m not going to cry,” she said with determination. “I’m ready for your cock, Brad. Go slow, please!”
Brad’s cock was rock hard. He slathered it with lube, feeling the coolness against his skin. He knelt behind her and guided the tip to her slippery back hole. She was so tight he thought he might not get in. “Ready?” he asked one more time.
“Yes,” she said, her voice firm. “Do it.”
Brad took a deep breath and pushed. Her tightness was like nothing he’d ever felt. Pumpkin’s body tensed, and she let out a whimper and turned to look at him. He paused, watching her face. She nodded, biting her bottom lip. “Keep going,” she whispered.
He pushed again, feeling her body stretch around him. She was so tight, it was like trying to fit into a glove that was a size too small. He went slow, feeling her adjust to his girth. He slid in deeper, watching her face contort and he didn’t know if it was pleasure or pain. When he was fully seated, he leaned over and kissed her back. “Oh, Pumpkin, I can’t believe how good this feels. Thank you!”
Her voice was muffled by the pillow, but Brad could hear the relief in it. “I’m okay,” she murmured, “Don’t go fast yet. I need to get used to it. Why did I have to pick a boyfriend with a big cock?” she laughed.
Brad felt a sense of pride at her words. He knew he was well-endowed, and the idea of being the one to take her anal virginity was something he never thought would happen. He pulled back slowly, feeling her tightness cling to him, then pushed back in with the same slow rhythm. Her groans grew louder with each stroke. He could feel her body struggling to open up for him. He watched her face, seeing the signs of pain, he wanted to stop but her mom said he couldn’t.
He reached around and pulled her breasts out to each side. He pinched her nipples. “Is that better?” he asked, his voice strained.
Penelope nodded, her eyes fluttering shut. “Yes,” she murmured, “it’s helping. Oh, god, I don’t think I can keep going.”
“You heard your mom, we have to.” Brad was getting lost in the moment. He began to pick up the pace, his cock sliding in and out of her ass with more force. It was raw and primal, and he couldn’t believe he was fucking Pumpkin’s ass. He reached around and found her clit, rubbing it gently as he fucked her. She gasped, her body jolting at the sensation.
“Oh, Brad,” she moaned, “It’s too much! Take it out!”
He grabbed her hips to hold her in place. “I’m close, hang in there!” She was crying and it made him feel sorry for her. Her soft body was made for his cock, and he was more than happy to give it to her. He leaned down and kissed her neck, his teeth grazing her skin. “You’re doing good, Pumpkin,” he murmured, his breath hot on her neck. “Your mom would be proud.”
Penelope’s body tensed up around him. “Hurry, Brad, come in my bum!”
Brad’s strokes grew erratic. The idea of filling her up with his cum was too much. He watched her ass cheeks jiggle with each thrust and felt his balls tighten. “Pumpkin,” he groaned, “I’m gonna come. Right now!
“Do it!” she yelled, her voice strained. “I want to feel it!”
Brad’s entire body tightened as he thrust into her one last time, his cock releasing a flood of hot cum deep inside her ass. She collapsed to the bed and he held her tightly as he continued to come, his body shaking with the intensity of his climax. For a moment, her mom ceased to exist, and it was just the two of them, locked in this intimate embrace.
He didn’t want to pull out. Pumpkin lay under him, panting and trembling. “Did I do good?” she asked, her voice small and vulnerable.
“You were amazing,” Brad assured her, kissing her neck. “I’m so proud of you.”
He pulled out gently. “Don’t move,” he said reaching for the phone. He took several pictures of Pumpkin’s red anus with his cum leaking out. He sent them to her mom. He knew he had to play by her rules if he wanted to keep seeing Pumpkin. The phone dinged with a return text. “Good boy,” it read, followed by a devil emoji.
Pumpkin reached back and rubbed her bum. “It hurt,” she said, her voice shaky, “but not as much as I thought it would.” She looked at his large cock. “I can’t believe you got all of “that” in me!” she giggled.
“I can’t believe it either,” Brad said with a grin, feeling a strange sense of accomplishment. He leaned in and kissed her gently. “Your mom still wants me to fuck your pussy. I need to clean up and then you can suck me hard.”
Penelope’s eyes widened at the thought of sucking a poopy cock. “Clean it good,” she said, still feeling the burn in her ass. But the idea of pleasing Brad and her mom won out. “I need to rest for a minute, I’m still hurting.”
Brad nodded, feeling sorry for the pain he caused. In the bathroom his mind raced. The power dynamics were twisted. He was the one being blackmailed, but at the same time, he felt like he had the upper hand because he had a cock that they both wanted.
When he returned, Penelope was masturbating. Her eyes were closed, and she was lost in the sensation. Brad got on the bed and rested his cock on her chin. “Pumpkin, you’re the sexiest girl in the world!”
Penelope looked up at him, her eyes glazed with lust. She opened her mouth, and he slid his cock in. She smelled her bum but she didn’t taste anything. “Mmm,” she moaned closing her eyes. She loved the feeling of his cock in her mouth. Brad took her breasts in his hands and squeezed them, feeling them bounce with each thrust into her mouth. She needed to come so bad.
Brad watched her masturbate while he fucked her face. He went soft after their anal session, but her mouth was heavenly. He felt guilty about the whole situation with her mom, but the sexual thrill overpowered his conscience. He wondered what else her mom would make him do.
Penelope’s hand worked her clit. His cock was maxed. She was close to coming. She moaned around his shaft and her eyes rolled back in her head. He pulled out, her saliva coating his length. He spread her legs. “It’s time, Pumpkin,” he whispered.
Pumpkin nodded. Brad opened the condom package and rolled it down his hard cock. Penelope was still sore, but she held out her arms in welcome. She bent her knees and Brad climbed into the saddle. His lips met hers and she sucked on his tongue as his cock teased her pussy. “I want you so bad,” she trembled. “But go slow, baby.”
With both hands on her magnificent breasts, he rocked his hips, touching but not penetrating her virgin pussy. Her beautiful face strained to smile at him. “You’re so beautiful,” he murmured. “Thank you for letting me be the first.”
“Oh, Brad, no more teasing,” she whimpered. “Please, I want to feel you inside me.” Her hips rose to capture his cock, but the tip kept sliding over her wetness.
“Reach down and guide me.” He took a moment to appreciate how she quivered when the tip breached her entrance.
Her hand shook and she changed her mind, gripping him tighter to prevent his cock from going deeper. “I’m scared,” she whispered gazing into his soft blue eyes. “My bum is still hurting so bad! Will the same thing happen to my pussy? Mom said it would feel good! It doesn’t!”
Brad kissed her lips “No, Pumpkin, this is different. But I’ll go slow. If it hurts too much, I’ll pull out. I promise.”
It took all of her internal strength to release his cock. She nodded, trusting him, as Brad gently pushed, she squeezed his shoulders. Brad’s eyes were filled with love and concern, it made her heart melt. She winced as he stretched her flesh open. It was a different kind of pain than anal sex, she clenched her teeth. The head of Brad’s cock slipped in then stopped at her barrier. “Oh, Brad,” she gasped unable to stop the tears forming in her eyes.
Brad kissed her nipples. “Ready, Pumpkin? I can go slow or fast, like when you rip off a band-aid.”
“Fast,” she whimpered, closing her eyes in anticipation of the pain.
“No, look at me, Pumpkin,” Brad said softly, wiping a tear from her cheek with his thumb. He waited until she opened her eyes and met his gaze. “I want you to remember this moment for the rest of your life with fondness, not fear. Now, take a deep breath and let it out slow.”
She took a deep breath and nodded. “I’m ready.” Brad pushed his hips forward and the tip of his cock broke through her hymen. “Fuck!” she exclaimed letting out several sharp gasps.
“You okay?” he asked holding still. He didn’t want to hurt her further.
“Yeah,” she panted, wrapping her legs around his waist. “I pictured it more painful in my mind. Thank you for being so caring.”
Brad looked down and saw her virginal blood. He forgot to put a towel down. He didn’t know what he would tell his mom, but he didn’t want to stop. “Keep looking at me, Pumpkin,” he whispered, pushing in inch by inch. “You’re so tight. It’s the most amazing feeling ever.” He kept going until he was fully inside her.
“Oh, Brad,” she whispered. “I didn’t think it would fit.”
He waited for her to adjust to the feeling. It took a supreme effort to hold himself still. “Okay, Pumpkin, I’m going to take this slow,” he assured her.
Her eyes never left his. “Okay,” she whispered.
He began to move in a gentle, rhythmic motion, feeling her pussy stretch and adapt to him. With each stroke, she grew wetter, easing the way for him. He watched her face for extreme discomfort. Her eyes never left him, and he felt her relax slightly.
She began to move her hips in sync with his, and her face broke into a smile. “It feels ... good,” she murmured in amazement. “Mom was right! Go faster, Brad, fuck my cunt!”
Her language should have shocked him, but it didn’t, Pumpkin was full of idiosyncrasies. Her facial expressions changed to match the intensity of his thrusts, her eyes fluttering and her mouth parting in silent cries of pleasure. Brad picked up his pace, feeling her tightness clamp down on him with every stroke. He was glad he fucked her ass, otherwise, he would have come by now. Her pussy was heavenly, warm, wet, and inviting. “I want to do this to you every day!” he whispered in her ear.
Her cheeks flushed. “Me too,” she breathed, her eyes fluttering at him.
Brad felt his love for her swell as he watched her come to life underneath him. Her moans grew louder, and her hips began to meet his thrusts with more urgency. The room was filled with the sweet sound of skin slapping against skin and the wetness of their union. The scent of sex and Pumpkin’s sweet yips filled the air.
They found their rhythm, and Brad’s strokes grew stronger and more intense. He watched her face contort in ecstasy, her eyes never leaving his. He knew she was close, her pussy walls contracting around his cock. He reached between her legs and found her clit, rubbing it in time with his strokes. “Cum for me, Pumpkin,” he groaned. “I want to feel your sweet pussy milk me.”
Her eyes went wide and she threw her head back, crying out as her orgasm crashed over her. Her body convulsed around him, her pussy squeezing him tightly. It was more than Brad could handle. With one final deep thrust, he came inside her, thankful he had a condom on. They stayed connected, both panting and trembling with the aftershocks of pleasure.
Penelope’s body went limp, and Brad could feel her muscles relax around him. He kissed her neck. “You’re mine, Pumpkin,” he murmured, feeling possessive. “I’m the only one who gets to do this to you.”
She nodded, still lost in the aftermath of her orgasm. “Yes,” she whispered. “I never want anyone but you.” Her arms hugged him to her chest and she sighed contentedly. “Hm, I could stay like this forever.”
But they had to move. Brad knew Mrs. Westbrook would be expecting an update. He pulled out, the condom was full of cum. Penelope let out a shriek. “Wow! I’m glad that didn’t go in me!”
He chuckled and kissed her forehead. “I’m not,” he said, “but we need to wait until you’re on the pill.”
“Don’t forget to take a picture of my bloody pussy and send it to Mom. She’ll want to see that,” Pumpkin reminded.
Brad nodded. He didn’t want to, but he knew he had to play along. He took a deep breath and snapped the picture, sending it to Mae with the text, “Pumpkin’s cherry is no more.”
The phone beeped with a return message almost immediately. Brad was conflicted by the knowledge that Mae was getting off on this. He couldn’t deny the thrill of the taboo situation, but he also couldn’t ignore the guilt that gnawed at his conscience. “Your mom says congratulations. I can’t believe she wanted to see that.”
Pumpkin was still floating. “I’m not a virgin anymore. I’m a woman now.” She giggled. “Mae’s not my real mom, Brad. She’s my stepmom.”
“What?” Brad responded in confusion. “Mae is your stepmom? But...” He trailed off, realizing that the implications of this revelation were significant. It didn’t change the fact that he had just took Pumpkin’s virginity with her stepmother’s consent, but it did add another layer to the tangled web of their relationship. “There’s something I need to tell you.” Brad hesitated knowing this might end things between them, but she deserved to know the truth about him and her stepmom.