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Greg & Rochelle's First Time

Summary:

Short fic where Greg asks his older brother, Wirt, for advice about how to make love for the first time with his girlfriend, Rochelle (OC Sara's younger sister who I created for my fic "Growing, running and stumbling"), set around 10 years in the future, with Greg being 16. Wanted to write this fic for Valentine's Day. Includes sexually explicit material, if it makes you uncomfortable it's best not to read. Thank you.

Notes:

(See the end of the work for notes.)

Work Text:

Greg and Rochelle's first time

Greg, Wirt's younger brother, and Rochelle, Sara's younger sister, were the same age and had become good friends after their older siblings started dating and then became teenage parents to Elaine. They had grown up together and, as expected, had also fallen in love. To Greg, Rochelle was an absolutely beautiful and sweet girl who always supported him and joined in his adventures. To Rochelle, Greg was that sweet boy who always worried about her and looked out for her. Now, they were both 16 and, just like their older siblings when they were that age, felt a surge of hormones that urged them to be close to each other as much as possible. They had started slowly, tentatively rehearsing their displays of affection, until they were confidently sharing kisses, caresses, and hugs when they were alone. They already knew that to release those sexual urges that were beginning to overwhelm them, they resorted to masturbation while fantasizing about each other, but they were now beginning to wonder if it was time to finally make love for the first time.

One day, Greg went to ask his brother for advice, who at first couldn't help but be surprised to learn that his sweet and innocent little brother had already grown up and wanted to take that big step with his partner as he had done at the time with Sara.

- "I think Rochelle and I are ready to go all the way, Wirt, or at least we want to try."

- "And how are you feeling?" Wirt asked him.

Greg shrugged and said:

- "Excited, a little nervous, like when I was going to participate in the school musical and I didn't know if I was going to sing well, do you remember?"

- "That sounds very familiar," Wirt replied with a confident smile.

- "I don't want to do it wrong, I don't want her to feel uncomfortable. Is it true that it hurts for girls the first time? I don't want to hurt her by accident, nor do I want her to think that only I want to enjoy it."

Wirt turned to his brother and answered him confidently.

- "You're doing great. If that worries you, it's because you really care about Rochelle. Look, Greg, if you can stimulate her the right way, caressing her whole body and whispering sweet nothings while kissing her and touching her gently, like she's an instrument, it's less likely for her to hurt when you enter her. The important thing is to tell her how much you love her and go slowly. You'll soon feel like speeding up, and you'll both enjoy it. Don't worry if you finish before her; it happens sometimes. Remember, penetration isn't the only way to give a woman pleasure. Talk to each other before, during, and after. Express what you like and how you like it.""

- "What if something doesn't feel right?" Greg asked.

- "Then you stop. You or she, without blame or pressure, trust isn't broken if you or she says "wait".

- "Rochelle says she trusts me a lot and wants us to show our love this way," Greg replied.

- "Then you should trust her too. It's not like it's an exam you have to pass, it's an experience you're both going to share," his brother replied.

Greg smiled, feeling more at ease.

- "You always make everything sound less scary, Wirt."

"You don't have to do it perfectly. You just have to be yourself, and take care of her and love her like you always have," Wirt replied.

- "Hey, Wirt... what if things go... weird?"

- "It means it was all human and natural, and that's okay, Greg. I'm glad you trust me enough to talk about this. Just remember, don't forget to use a condom and make sure it's not defective, because you could unintentionally repeat what happened to me with Sara and become a father very soon," Wirt said, with a hint of concern.

- "Another question, Wirt, and I hope you don't take offense, do you regret that Sara got pregnant by carelessness and Elaine was born?" Greg asked him with complete honesty.

- "It was unexpected and life-changing, but no, Greg, I don't regret it. Accidents happen, and sometimes, as the great Bob Ross said, they're happy accidents. I wouldn't trade my daughter for anything in the world, and I'm sure you wouldn't either, with how much you love her and how much she loves you. But everyone is different, and it's best to let things happen in their own time."

- "That's right, Wirt, I love my niece very much and I'm glad she's with us. I will, in fact, I've already practiced using it."

- "That sounds great, Greg. Remember, I'm always here for you whenever you need anything. Have fun and enjoy the magic of love; believe me, it's the most beautiful feeling a person can experience," Wirt said, giving him a warm hug.

- "Thank you so much, brother, you're the best brother anyone could have, and that's a rock fact," Greg said, laughing.

A few days later, Greg and Rochelle walked home from school hand in hand, having already made their decision. They both told their parents, who gave their blessing and told them to enjoy it, obviously using protection. At that moment, only Wirt, Sara, and Elaine were home, and knowing that their younger siblings wanted to be intimate, they agreed to let them be alone in Rochelle's room without interrupting them, while Sara took Elaine to the mall. Rochelle led Greg to her room and gave him a passionate kiss on the lips. The room was beautifully arranged, with low lighting and soft romantic music playing from a speaker. The two teenagers gazed into each other's eyes, filled with desire and passion.

- "Can I have the first dance, Greg?" Rochelle asked her boyfriend in a sultry voice.

- "Y-yes, you can, baby," the boy replied, nervous but determined.

The couple embraced and began kissing as they had hundreds of times before, delicately tracing each other's lips and using their tongues, their saliva mingling in each other's mouths. Instinctively, Rochelle began tracing Greg's neck and nape with her fingers, while he ran his fingers over his girlfriend's shoulders and timidly touched her brown skin. Their passion grew, fueled by the soft music playing in the background. Rochelle encouraged Greg, guiding his hands to her firm breasts. He blushed, but remained focused, continuing to kiss her, his hands exploring her breasts through the pink t-shirt that accentuated her curves.

The girl trailed her lips down to Greg's chin and then to his neck, continuing to kiss him, intensifying his passion. Greg brought his lips close to Rochelle's ear, sighing sensually as his hands traveled down to her waist and hips. Rochelle began to remove her shirt so he could continue exploring her skin, and he, too, removed his shirt, feeling the heat. Rochelle sat on the bed, and they both took off their shoes and lay on top of each other. They whispered sweet nothings and continued to caress each other passionately, Rochelle inhaling the scent of her boyfriend's cologne and Greg inhaling the sweet perfume she wore.

They both felt their hearts beating faster and their bodies growing hotter. Rochelle wrapped her legs around Greg's hips, pulling him closer, making him feel his already erect member brush against her crotch through her clothes, both of them moaning at the contact of their bodies.

- "Greg... mmmh... I love you, keep going, I like it a lot" - Rochelle said in a voice that was already beginning to be dominated by her carnal desire, which stimulated the boy even more.

- "Oh, Rochie, I love you too, and I want you so much, baby," Greg replied between sighs of pleasure.

Rochelle was there, dressed only in a white undershirt, which she removed so Greg could see the purple bra she was wearing, thinking of her boyfriend, as she knew it was his favorite color. They continued kissing and caressing each other, showing everything they felt for one another. Greg unbuttoned his jeans because they were getting in the way, and Rochelle couldn't help but giggle when she noticed the bulge in his underwear. Greg felt a little embarrassed, but this didn't last long when the girl gently caressed his member through his clothes, making him moan.

- "Oh, Rochie, that feels really good," Greg said, aroused.

Rochelle proceeded to remove her sweatpants so Greg could see her panties, the same color as her bra. The boy's heart raced, and he positioned himself over Rochelle again to continue their foreplay. Greg reached behind his girlfriend and tried to unhook her bra, but seeing that he was having trouble, Rochelle showed him how. Greg felt a little embarrassed that he hadn't been able to do it himself, but his girlfriend encouraged him to touch her bare breasts. They weren't very large, but they weren't small either. Greg explored them coyly, and the delicate touch of his fingers was enough to make Rochelle let out soft moans of pleasure, which turned Greg on even more and made him feel proud to know the most sensitive spots of his beloved.

- "Oh, Greg, ah, keep going, it feels so good, ah" – Rochelle said between moans, letting out the pleasure she felt.

Greg mustered his courage and began kissing Rochelle's breasts, tracing her nipples with his tongue, giving his girlfriend even more pleasure. The two looked at each other, and Rochelle guided Greg's hands to her panties, lifting her hips so he could remove them. When he did, Rochelle spread her legs, giving Greg an unforgettable view of her most intimate area, surrounded by pubic hair and glistening with the moisture already present inside. Greg was stunned for a few seconds, and then timidly asked:

- "Rochie, can I touch you there?"

- "Yes, Greg, touch me, let yourself go," his girlfriend replied lustfully.

Without further thought, Greg began to gently explore Rochelle's vagina. He remembered what his brother had told him and touched the small bump at the top. Rochelle moaned and arched her back at the sensation.

- "Greg, I love you! Don't stop, please!"

Greg kissed Rochelle's lips again to stifle her moans and continue stimulating her, sliding his finger down to insert it into her vagina and feel how wet she was. Rochelle kept repeating Greg's name between moans. The boy finally pulled down his underwear, freeing his fully erect penis, ready for action, and Rochelle took it in her hand, stroking it from top to bottom, just as she imagined he did when he masturbated thinking of her. Pleasure overwhelmed Greg, and he let out soft, sensual moans. They continued masturbating each other for a few minutes, until finally they looked at each other, ready to unite their bodies as one. Before that, Greg quickly took a condom from his pants pocket and carefully put it on.

- "Are you ready, baby?"

"Yes, Greg, I am. Make me yours and make me come," Rochelle replied, incredibly aroused.

- "Of course, Rochie. I'll go slowly and it might hurt a little, but I'll be careful, okay?"

- "Yes, Greg, thank you."

So, the couple kissed once more, and Greg slowly brought his erect penis to Rochelle's vagina. He began to penetrate her slowly, feeling a small barrier that prevented him from entering. Looking at Rochelle, whose gaze was full of desire and passion, Greg gave a slight thrust with his hips, breaking his girlfriend's virginity and entering her completely, feeling surrounded by Rochelle's soft, moist walls. The girl let out a soft moan of pain as she dug her nails into Greg's back and wrapped her legs around his hips.

- "Are you okay, Rochie?" Greg asked, sounding worried.

- "Yes, Greg, it hurt a little, but I'm fine now. You can move, but please be gentle with me."

Rochelle's sweet face and the way she said it encouraged Greg to continue, and he began rubbing his penis against his girlfriend's insides, slowly at first, but he started to go faster as the tingling sensation increased, giving them both immense pleasure. Rochelle traced Greg's back with her fingertips while he panted in her ear and inhaled the sweet scent of her hair.

- "Ah, Greg, keep going, ah, I love you, ah, aaaaaah" – Rochelle moaned, letting herself be carried away by a pleasure she had never experienced before.

They kissed, noticing how their kisses now tasted so much more delicious, combined with the sensation of being inside each other. They kissed slowly and passionately as the music continued to play, and it was as if nothing else in the world mattered, only the love and pleasure they both felt as they moved in unison on the bed.

Rochelle's moans of love turned into cries of pure pleasure, urging Greg to quicken his thrusts as she shuddered beneath him. They continued to lose themselves, whispering "I love you" in each other's ears, and soon Greg was accelerating his movements, just as Wirt had told him it would feel. They were both in paradise; they had never felt anything like it. After a few minutes, Greg began to feel something wanting to come out of him, and Rochelle's vagina contracting around his penis only intensified that sensation. Rochelle was still enjoying herself, and she too began to feel her own climax approaching.

- "Oh, Greg, aaaah, I, I think I'm going to...aaaaah, aaaaaah!"

- "Baby, Rochie, me too, I can't hold it anymore, I love you, Rochie! Potatoes and molasses!" Greg replied, on the verge of orgasm.

- "I love you, Greg! Aaaaaaaaaaaaaaaaaaah!" Rochelle screamed as she reached climax at the same time as her boyfriend.

- "Rochie! Aaaaaaaaaaaaagggggggggh!" Greg grunted as he finally ejaculated inside the condom when his girlfriend's vagina milked his penis, followed by passionate gasps as he collapsed onto her chest. She hugged him tightly after they had reached paradise together, both panting in absolute satisfaction.

- "Rochelle, that was incredible," Greg said, still trying to catch his breath. "Now I know how Wirt feels when he does this with Sara."

- "Yes, Greg, I think I now know why they love doing this. It felt so good, and I don't want to do this with anyone but you, my love. I'll never forget this," his girlfriend replied, with a smile.

- "Me neither, and you're also the only one I want to make love to."

Greg finally pulled out from her and removed the condom, which was intact with his semen still inside. The two embraced under the sheets, sharing their warmth, their faces glistening with sweat but beaming from ear to ear, their hearts overflowing with love. Rochelle snuggled against Greg's chest, playing with her lover's chest hair.

- "I'm glad we were each other's first time, Greg," Rochelle said, satisfied.

- "And this is just the first of many times together, Rochie, because we're going to be together for the rest of our lives," her boyfriend replied.

- "Of course, love."

The two shared one last kiss and lay back, relaxed and filled with love. They fell asleep for a while. Without them noticing, Wirt carefully opened Rochelle's bedroom door and saw his little brother, who was now a man, sleeping peacefully in the girl's arms, and he felt a surge of joy for him.

A few hours later, the couple woke up and went to the dining room, where Wirt, Sara and Elaine were already preparing dinner.

- "Hi, Greg, and hi, little sister, did you have a good time?" Sara asked with a hint of mischief.

- "Oh, yes, Sara, it went very well," Greg replied, blushing. Rochelle giggled.

- "I just hope you used protection, we're not ready for another little one running around the house yet," Sara said, joking and speaking seriously at the same time.

- "Don't worry, sister, we already know how to do that," Rochelle replied proudly.

- "By the way, Wirt, can I talk to you?" Greg asked.

- "Sure, let's go to the living room while Sara finishes making the potato pancakes," his older brother replied, and they both left the kitchen. Once in the living room, Wirt noticed his little brother's expression: he looked tired, but happy, as if he had finally managed to climb the tall rock climbing wall of the shopping mall that he had been so afraid of as a child.

- "How did it go, Greg? Did you enjoy it?" Wirt asked somewhat hesitantly.

Greg took a breath and answered calmly.

- "It was... strange, good, weird, beautiful, all of that together."

- "That sounds pretty realistic, Greg. But you enjoyed it, and so did Rochelle, right?"

- "Yes, we both liked it. I got a little nervous, um, I couldn't use my hands to take off her bra and she showed me how to do it, she was patient and encouraged me to start slowly."

- "I'm glad to hear that, Greg. Making love isn't something you learn the first time; you have to get to know each other, it's something you experience, that you explore, sometimes it can take years."

- "Being inside her feels incredible, it's almost like you can hear her heart beating from the inside," Greg said, smiling broadly. "And that feeling of finishing, it's different from doing it yourself with your hand, if you know what I mean. It's like I took a direct, nonstop flight to paradise."

- "I know, Greg. Nature designed us this way for a reason, to provide us with pleasure and also for when it's time to reproduce. How did you feel about the famous afterglow?" Wirt asked.

- "How did you felt it the first time you made love with Sara?" Greg replied with another question.

- "Weird, but nice. It wasn't something grand like in the movies, but I felt that she and I shared something, the way we love each other and showed our love using our most intimate parts. It's kind of like when you stay up talking to someone late and you don't want it to end, and all that matters in that moment is the well-being we both feel, inside and out. We stayed embraced, without any rush. You just think, " Ah, that's what it feels like ," and there's nothing more."

- "Well, I think I felt something similar. I remembered that song you had on one of your albums, the one about the boy who took a woman's hand and saw the sun rise like a man," Greg replied.

- "Good old Bobby Goldsboro gave us great advice, Greg. I'm so glad to hear you enjoyed it—well, that you all enjoyed it—and the love you and Rochelle share. Remember, I'll always be there for you whenever you need good advice, whether it's about this or anything else," Wirt said, hugging his little brother.

- "That's what I'll do, Wirt, thanks for everything," Greg concluded, and both brothers returned to the kitchen to have dinner with Rochelle, Sara, and Elaine.

END

Notes:

In case you're wondering, I named Rochelle after the Win or Lose character of the same name.