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Remaining quiet, you stand up from your seat and walk around the table and next to Olivia. You offer her your hand. She takes it and stands up, looking confused. And she’s even more so when you hug her tightly by the waist and kiss her deeply.

Her legs lose strength, so she hugs your back to support herself as she simply lets you kiss her.

“Don’t look away from me.” You tell her firmly after breaking the kiss and seeing her look to the side. “What happened to not regretting what you did?”

“…” She grimaces.

“I’ve known from day one that you three aren’t saints.” You tell them. “I know firsthand that you’ve done some pretty nasty stuff. But we’re here now because I’ve accepted it. So don’t be ashamed of telling me these things. If anything, I’m more annoyed that you’re so disgusted about your first time.”

“Maybe that’s just what I deserved…” She mutters.

“Stop the self-deprecation.” You tell her. “That’s not you, is it? It doesn’t matter that your first time sucked, because you’re with me now.” You say, looking deep into her eyes. “I’m gonna make you forget all about that time.”

You hear Lilian and Jessica giggling behind you, and you see Olivia blushing madly.

She grins. “Well, aren’t you a hot stud.” She hugs you tightly and rests her chin on your shoulder. Her body relaxes and you hear her take a deep breath. “Thanks.” She mutters honestly and kisses your cheek.

And suddenly, you feel another set of big breasts pressing against you from behind as Jessica joins the hug. “Why don’t we take you up on your offer right now, then?” She says with a mischievous grin.

“R-Right now?” Lilian asks, slightly anxious.

“It’s not like this is a spur of the moment, right?” Jessica asks. “It’s what we came here for, but things got a little heavy.”

“Wait.” You say, understanding the implications. “You mean, you three…?”

“We’ve been making such a big deal out of you dating the three of us that it just seems right, you know?” Olivia shrugs, but you can tell she’s just trying to look disinterested.

“I-It was Sophia’s idea!” Lilian says.

“Of course it was.” You say, shaking your head. “But I’m not going to force anything on you. We’ll do it when you’re ready.”

“David, we ARE ready.” Jessica giggles. “You saw the scores. Even Lilian wants it.”

You break the hug with Olivia and Jessica and turn to the blonde girl. “Are you sure?” You ask her.

She takes a deep breath and stands up from her seat. She walks up to you, standing firmly and looking into your eyes. “Kiss me.” She says.

You can’t help but chuckle a bit first before you comply. You put a hand on her cheek and lock your lips with hers. She moans when you slip your tongue inside her mouth. She hugs you tightly and returns the kiss eagerly before pulling away after nearly a minute.

“Virginity’s overrated anyway.” She grins nervously.

“Sorry. That’s not gonna work for me.” You tell her, stroking her cheek with the back of your fingers. “I want you to be sure this is something you want.”

“David, you’re seriously asking me if I want to have sex?” She asks you with an annoyed frown. “Of course I want to! Yeah, I’m nervous, but that’s obvious. It’s my first time! I… might just be starting to understand what it means to be in love, but the fact that I want to have sex with you hasn’t been a question for a LONG time. I only refused last time because you needed to go on dates with Jessica and Olivia, first.”

“It’s the same for us.” Jessica says, leaning in to kiss your cheek. “The others all had something different to say about losing their virginity, so I’m still a little nervous.” She giggles. “But I’m excited, too. I’m sure you know girls want it just as much as guys do.”

Olivia then hugs you from behind, giggling in your ear. “You don’t seriously expect me to stay calm after you tell me you’ll make me forget my awful first time, do you?”

“Ahahaha…” You chuckle nervously. “Believe me, it’s not that I don’t want to. It’s just that, even though the three of you are beautiful and sexy, I don’t want you to believe I want you just because of that.”

“You’ve made that clear already.” Jessica says, kissing your neck and making you shiver. “We’ve all been holding it for long enough, right? We like you, you like us, we all want it and we’ve talked enough about it.”

“Alright. Alright.” You sigh contently. “It’s not like I need that much convincing, anyway.”

“Oh. And just to you know…” Olivia says. “We’re all on the pill.”

________________________________________________________________

After stripping down to your boxers in front of the girls, you sit on your bed with legs crossed and watch them slowly remove their own clothes. They do it slowly, and it’s kind of amusing to see them acting so bashful. They’re very aware the you’re looking and try not to meet your eyes.

“D-Do you need to stare so much?” Lilian asks.

“Yes. I like the view.” You nod shamelessly.

“You’ve seen many women naked already.” Olivia pouts. “It’s not like this is anything new.”

“Of course it’s new! I’ve never seen you naked.” You insist. “Hey, you were the ones pushing for this.”

“Ugh! He’s right!” Jessica says. And pumping herself up, she throws away her shame along with the rest of her clothes, save for her underwear. She stays in her high cut, black lace panties and matching black bra. Her skin, being slightly darker than the others’, gives her an exotic and sensual aura that’s already making you hard at the prospect of being with her.

“There! If you girls take too long I’m gonna hog him for myself!” Jessica giggles and skips toward the bed, sitting next to you and hugging your arm as she gives her friends a teasing smirk.

“Oh, you bitch.” Olivia grins and starts undressing faster as well. She also stays in her underwear, a matching set of lightly pink lace panties and bra with blue straps. Her skin has a slight, tasteful tan to it and her figure is just the perfect mix of slender and curvy. She takes her seat to you right, grabs your hand and pushes it against her large tits. “Let’s continue from where we left off the other day.” She says breathily.

Not wanting to lose to her friend, Jessica grabs your left hand and pushes it against her own chest. “You went farther with her than you did with me. I think I deserve some attention too.” Jessica giggles.

Good to see that they’re taking this as playful competition instead of getting angry about it. However, even though you’re in heaven for having your hands in the bosoms of two of the sexiest girls in the fucking planet, there’s another person you want to focus on first.

“Come here, Lilian.” You tell her with a smile.

“S-Seriously?” She asks. “Y-You’re asking me first? W-Why?”

“Because I want you first. Why else?” You chuckle.

“…” It’s faint, but you want to believe she’s happy about your words. She smiles excitedly before she shakes her head and removes the rest of her clothes. She looks down at herself, most probably down at her plain, beige bikini panties and bra, then back at her friends before she smirks and decides to lose the underwear, too.

Olivia and Jessica laugh at her one-upping them, but you’re too busy ogling her figure. She’s slender and less curvy than Olivia, with a build more similar to Emily’s, if less toned. Her breasts are about her size, as well. Perfect handfuls. Her straight, light blonde hair cascades down her shoulders. She swallows and walks up to you without breaking eye contact.

“Happy?” She asks.

“Very, very much so.” You tell her with a shy grin.

Your hands leave the other two girls, but they don’t protest. You lay back on the bed and give the girls an inappropriately innocent look. “Mind helping me out with this.” You say, eyeing your boxers.

Lilian swallows, but hooks her thumbs at the edge of your boxers and slowly pulls them down your legs, revealing your semi-hard length.

“O-Oh.” The blonde mutters, blinking several times.

But when you think that they’re going to say something about your size, your chest tightens when you instead see all three girls grimace, with Lilian and Jessica looking Olivia with worry.

“I sense an issue here.” You sigh, sitting up.

“N-No!” Olivia immediately says. “It’s just… I was hoping… you’d be… smaller.” She admits with a wry smile.

“We shouldn’t bring this up now, but…” Jessica starts. “You see, that math teacher, he was…”

“Olivia says he was big, too.” Lilian says. “And that it hurt her.”

Oh.

Well, fucking hell.

“B-But hey, these are totally different circumstances!” Olivia says, smiling and trying to relax. “We’ll just have to try, r-right?”

You try your best to prevent yourself from showing much concern, simply because Olivia seems to be pushing herself so hard. You don’t want her to do anything she’s not ready for, but the thing is she IS ready, she wants this, she’s just worried it’ll be a repeat of her first. And at the same time, you have to find a balance easing everyone’s concerns.

You let out a soft breath, lean in and give Olivia a soft peck on the lips that lingers for only a few seconds.

“W-Wha…?”

“Going all three at the same time might have been a bit too much.” You chuckle. “But we’re already here. Do you girls mind if I focus on one at a time? We’ll have time to try other things later.”

“S-Sure.” Olivia nods with a small, relieved smile.

“I admit, I’m excited.” Jessica giggles. “Never thought it’d be like this.”

You notice Lilian’s face turning resolute. She looks at your penis and licks her lips in anticipation. “Alright. I’m ready. What do we do now?”

You sit at the edge of the low bed with your feet on the floor and pat your lap. “Sit here. Looking at me.” You tell her.

Lilian’s legs are trembling slightly as she sits on your lap, and she flinches when your cock brushes her stomach. You hug her by the waist and rub her back, at the same time pushing her towards you so her chest is pressed against yours.

“Relax.” You tell her, kissing her cheek. “If at any point there’s something you don’t like, tell me. I mean it. If this doesn’t feel good for you, we stop.”

“Okay.” She nods.

You lean in and kiss her. She doesn’t take long to open her mouth and let your tongue inside. She moans softly as you roll your tongue around hers, caress her shapely ass and fondle one of her boobs. She lets out a yelp when you pinch one of her nipples, but since she starts kissing you more deeply, you know she liked it.

You then position yourself so that the length of your cock is pressed against Lilian’s labia. She shudders and looks at you with a bit of worry. You answer by softly kissing her neck and moving your hips to grind your length against her.

She gasps, her mouth opened in a small O. She embraces you tightly as her body heats up and her pussy gets wetter and wetter. “Holy shit.” She gasps again.

You keep rubbing her back gently, kissing her shoulder and fondling her soft tits. You feel her relaxing in your arms and losing herself in the moment. She looks you in the eyes, her face flushed red, and leans in for another deep kiss. She slides her tongue inside your mouth this time. You’re feeling a bit lightheaded from the pleasure, too, but focus on your task as best you can.

You want to make this the best you can for her, show her that you care about her, and reassure her that sex, and especially a first time, doesn’t have to be like what happened to Olivia.

“You’re so pretty.” You whisper in her ear with a soft chuckle. “How did I resist you when we were trying out swimsuits?”

“I saw you looking at me,” She gasps. “I wanted this that day, too.” She admits.

“I want you, Lilian. I really do.” You say, staring into her eyes.

Her lips slowly curl into a grin as she stares back at you with those beautiful blue eyes. “I want you too. So take me. I’m ready.”

After another, shorter kiss, Lilian lifts herself and you start pressing the tip of your cock against her wet pussy.

“Don’t worry. Go as slowly as you need.” You tell her.

She nods and starts going back down, slowly but surely getting your length inside her. “Oh shit…!” She gasps and shudders at the feeling. You notice the moment her hymen is broken when she shuts her eyes and bites her lip.

“You okay?” You ask her, rubbing her back.

“I-It hurt.” She says with a wry smile.

“Is it too bad?” Jessica asks from behind you. Her tone worried.

“Just… give me a second.” She says, taking deep breaths. “I know I’ll start feeling good again in a moment.”

“Take all the time you need.” Olivia tells her, and you hum in agreement.

When she’s ready, she starts lowering herself on you again. Bit by bit, your whole length is going inside her, her pussy gripping you nicely letting you slide in without much issue.

“Oh fuck. Oh fuck. Oh fuck.” She gasps, looking up at the ceiling until she’s finally completely seated.

“H-How is it?” Jessica asks nervously.

“It doesn’t hurt anymore.” She grins. Her face is still red and she looks at you with excitement. “Alright, lover. Fuck me.”

She presses her lips against yours and starts moving her hips on her own. She goes slowly at first, with you matching her moves, but as she gets used to it she starts bouncing on your lap more aggressively.

“Yeah…! Yeah…!” She moans into your mouth as your cock stirs her pussy with every thrust. She holds onto the nape of your neck and leans back as if to let your dick go even deeper inside her. Her back arcs and she grinds herself on you. You hold her by the waist to support her while you keep thrusting up and inside her. The feeling of a new woman in your arms is always exhilarating.

“Oh shit!” Lilian stops bouncing, her body starts shaking violently as she orgasm rocks her to the core. Her pussy spasms around you, gripping you tightly and threatening to bring you over the edge as well, and you don’t resist it. You shoot your first load deep inside Lilian, making her gasp as a second orgasm hits her immediately after her first.

Feeling weak, she leans forward to rest against you. You slowly lay down on your back with your new lover on top of you. She breathes heavily, resting her head on your shoulder. After a moment, she lifts her head sluggishly and just… stares at you as if she’s seeing you for the very first time. She leans in and starts kissing you passionately and sloppily, moaning loudly and making wet sounds. Her hands roam your body, caressing you like she just realized she can do that.

You reciprocate, wrapping your arms around her and kissing her back. She doesn’t say anything. She kisses you for a long time, tasting your lips, your tongue and letting you taste her in return, loving every second of it. Minutes pass, and while you know you have to pay attention to the others, it’s hard to find the will stop her. This feels amazing. There’s something fundamentally different about the way she’s kissing you now.

But after waiting for a while, Jessica coughs to clear her throat. “Lilian. We want to do it, too, you know?” She says.

“Oh! R-Right. Sorry.” The blonde chuckles shyly. She looks down at you with a bright smile, brighter than you’ve ever seen her. She looks radiant, both because of the afterglow of her orgasms and because she looks genuinely blissful. However, she suddenly frowns and bites her lip, still caressing your arm.

You chuckle, put a hand on the back of her head and pull her face so that your foreheads and noses are touching. “From today on, we can do this whenever you want. I’m not going anywhere.” You say, gently rubbing your nose against her, making her smile return.

“Thank you.” She says with one last kiss. She swallows and gives you a shy, honest smile. “I love you.”

Your heart skips a beat. This is the first time she’s said that. Even Jessica and Olivia are giggling at hearing her admit it out loud. “I love you too.”

After one last peck on the lips, Lilian lifts her leg to get your dick out of her, and everyone’s eyes are locked to the string of cum still connecting you to her.

“Jessica’s next.” Olivia says, though her eyes are still looking at your hard, semen covered dick.

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