Chapter 17
Caleb
W aiting for Lily to enter the room and find the three of us felt like a lifetime of torture. My conscience kicked in. The sensible, sweet Caleb I knew I could be, or at least I hoped I was, had me questioning myself.
What the fuck was I doing here? What had I set Lily up for? I was supposed to be her best friend. I was supposed to protect her from guys like Jace and Damien. From guys like… me. Was I really just as bad as the two of them?
I took a breath and calmed myself. I knew how much she meant to me. How much she meant to all three of us. We were doing this for her, because we loved her. I convinced myself that this wasn’t selfish. That Lily had asked me to help her lose her virginity and overcome her fear of intimacy. She wanted to come to this party and get fucked.
By strangers. Fuck.
It's ok. We could be strangers for the night. All four of us. Strangers.
This is exactly what a real best friend would do. I was doing this with her best interests at heart. So the moment she walked into the room I knew exactly what I had to do.
She was nervous. I knew Lily and knew she’d be overthinking. Her stumbling into my arms as she backed away from Jace and Damien was typical Lily behavior. She stared into my eyes and directly into my soul, and for a moment, I feared she’d recognized me. She’d looked into my eyes a million times before– I needed to distract her so I crashed my mouth against hers and kissed her the way I’d always wanted to. The way I almost had back at her apartment. The kiss was deep and passionate. It wasn’t a kiss two strangers would ever share. I’m sure she felt my love for her with every movement of my tongue against hers. In my own delusion I’d been certain her kiss was reciprocal. That she'd kissed me back because she loved me too.
It hurt to know she didn’t kiss me as Caleb. She kissed me as the masked stranger. But at the same time I didn’t give a fuck because I finally got to kiss my best friend, and I hoped one day we’d share that kiss again, unmasked.
Jace soon had her on the bed, teasing her with his fingers. With Damien’s dick in her hand, and my mouth devouring her beautiful breasts, I told myself this was going better than I’d hoped. I’d always known Lily had perfectly round nipples. I’d tried not to stare whenever she didn’t wear a bra, especially when we’d been alone in her place and she was in her pajamas. Her thin camisole left little to the imagination. I’d never told her, and I was sure she was unaware of it, which made it that much more perfect to me. So sweet. So innocent.
As Jace thrust inside her pussy and Damien took her mouth with his dick I found myself moving away. I watched as they both worshipped her. Both of them flashed grins back and forth to one another.
Did they really care for Lily or was she just another pawn in their bitter rivalry and another way to have their egos stroked?
I paused.
Should I speak out and end it all? Should I tell her and damn the consequences? I’d lose her forever. She’d be all alone. She’d have no one.
Jace gestured for me to move back to the three of them. I hesitated and shot a look at Damien who reached out, grabbed my arm and pulled me closer. He took his cock from Lily’s mouth and pointed for me to replace it with mine.
Could I really go through with it?
A nod from Jace and the widening of his eyes told me I had no choice. Besides, I knew deep down I wanted to fuck her just as much, if not more, than the two of them combined. I’d grown up with my Lil bit.
I pulled my length from my boxer briefs and let them land on the floor. I didn’t need them restricting me. I also wasn’t going to do what Jace and Damien wanted. I wanted Lily next, and I wanted her pussy. I moved away from Damien and stepped closer to Jace. I looked at his perfectly defined torso and placed my hand against his chest. I could feel the erratic beat of his heart as I pushed him backward. He pulled his cock out from inside Lily’s sweet wet slit. I'd gotten my way.
He let out a grunt of frustration, but didn’t fight me on it. Instead, he moved toward her face. His cock rested against her lips while Damien moved position and groped her tits. He licked and sucked at her neck trailing his tongue along her collarbone.
Her moans told me she liked it.
I looked back down at my beautiful Lil bit, and placed my hand on her knee and pushed her legs apart. Holding my cock, I slid my throbbing head over her already soaked clit. I slapped my cock down harder and slid it up and down her wet pussy. I wanted so badly to fuck her, but I needed to make her want me to. I knew she said she wanted to be forced, but for my own sanity I needed a sign from her that said, ‘Caleb, take me’ .
I rubbed the head of my dick on her clit and slipped two fingers inside her pussy. She held tightly onto my fingers with her walls. Then she gasped loudly in pleasure and greedily stuck her tongue out for Jace.
She wanted this. Was that my cue to fuck her?
I zoned out and erased the image of Jace and Damien touching her. This was my moment with Lily.
I edged closer to her on my knees and held her legs open. Taking a breath, I thrust my cock roughly into her waiting pussy. I was done being gentle. I wanted to make her cry out for me. She shot her head toward me and looked down at where our bodies crashed into one another and then back up looking into my eyes with pure innocence.
The words of praise, adoration, of love, were right on the tip of my tongue but instead I let out a soft groan.
I couldn’t fuck it up. I wouldn’t.
This would be a night I’d never forget. The night I finally made love to my precious Lil bit.
I thrust harder, deeper, and pushed my fingers into her thighs. I knew I’d bruise them, and I wanted to. I wanted for her to come to me and show me those bruises from her night of mischief.
She felt incredible. Even better than I’d imagined every time I’d fucked her in my own fantasies. This was real. It wasn’t me staring at a selfie we took together and zooming in on her. This wasn’t my cock getting hard whenever she’d snuggle up to me during one of our movie nights and me having to hide it with a pillow. This was Lily and I, both freely fucking each other. I was fully aware Jace and Damien were pleasuring her too, but I focused on watching my cock slide in and out of her tight pussy and listened to her whimper out in pleasure with each increasing thrust. I knew she was responding to my cock and not the two of them since her moans remained in sync with every time my thick length hit her walls and found her G-spot.
Her legs shook in my arms and her heels dug into my ass.
Lily was finally free of her fear, or at least it seemed like in this moment she was.
But her lost fear only brewed my own.
I didn’t want to lose this.