Chapter Four
DEREK
Fortunately for me, my back was turned on Lilly as I led her upstairs. My eager dick hardened at the thought of finally having her to myself. I couldn’t scare her off this deal by being a complete beast. I had every intention of ruining her for that jerk off Jared. And to do so, I had to take my time and make this the best and hottest month of her entire life.
When I turned left at the top of the stairs, she tugged on my hand. “Where are you going? We can’t do this in your parents’ room.” When I turned back to face her, her eyes were wide.
“Well, I figured you didn’t want to go in the basement.”
“Yeah, I definitely would like to avoid whatever goes on down in your lair.”
She had no idea what my “lair” looked like. I wasn’t about to disabuse her of her presumptions, though.
“And we can’t fool around in Sarah’s room,” I said, motioning to my sister’s bedroom door.
Lilly shuddered. “Ew, no. You’re right.”
“Well, that only leaves my parents’ bedroom—which hasn’t been slept in for three years—or my mom’s sewing room. And I don’t really want to get down and dirty while surrounded by quilting supplies.”
She heaved a resigned sigh, and we walked down the hall. “Fine. It just feels like hooking up at a high school party.”
It was my turn to pause, standing still and tugging her hand to make her stop and look me in the eye. “You didn’t hook up at high school parties. Or did you?”
For some reason it was imperative to me that her innocent, good girl reputation from high school was true. It didn’t stem from some kind of old school misogynistic virgin fetish or anything. I just got a bit rageful at the idea of some pawing, eager high school dickhead talking her into a party shag.
She rolled her eyes at me, and I silently let out a relieved breath. “Of course not. You know I didn’t. That’s just what they always do at high school parties in movies.”
“Right,” I said, trying to mute the relief in my voice.
Upon arriving in my folks’ room, I led her by the hand over to the bed. I sat her down on the edge and stood in front of her. My plan was to merely scratch the surface with her. Leave her temporarily satisfied but wanting so much more. In order to accomplish this, I would not lay a finger on her no matter how much I was desperate to feel her soft skin or be the spark that made her breath hitch and her nipples harden.
Not tonight. Little by little. You have a month.
“So…why are you all the way over there?” She kicked off her shoes and sat with her back against the gray tufted headboard with her legs crisscrossed “What’s the plan?”
“I want to set a baseline tonight.”
“What do you mean, baseline?”
“I need to see you come, so I can learn your tells.”
Her cheeks pinked and she licked her lips, making it near impossible for me to stand my ground at the foot of the bed. But thankfully, I had the strength to stay in control.
“My tells? Like a poker player?” she asked.
“Something like that.” It might have been a burst of conscience or the effect of being on the verge of starting a physical relationship with the woman I’d fantasized about for years, but I found myself wanting to give her an out. “Are you sure this is what you want, Lil? It’s okay if you change your mind and want to stop.”
A cute little wrinkle formed between her eyebrows. “Why? Do you not want to do this? I understand if it’s weird or you’re not into me like that.”
Laughter escaped me before I could stop it. Her shoulders slumped slightly in what I could only guess was disappointment, and I felt like an asshole.
“Don’t you worry about what I want, Lush,” I said, drawing on my “DJ” mask to smooth things over. “I’m a dude. I’m pretty much ready for action 24/7.”
Sure, it was totally noncommittal and generic, but what was I supposed to tell her? I’ve been in love with you forever, and I never thought I’d have a chance to show you. Or it’s taking everything in me not to fall to my knees and worship at your feet even though you think I’m a joke. Best to keep things light with a little distance.
“So, what are you going to do to make me orgasm?”
Being a prim miss, I knew for certain asking that question was a victory for her. The word “orgasm” was probably the dirtiest thing she’d said in her whole life.
Well, buckle your seat belt my dear. I’ll have you filthy talking like a pro within the week!
“It’s not what I’m going to do. It’s what you’re going to do.”
“What?” she asked. The pink in her cheeks faded.
“It’ll be fine, Lush. You masturbate, don’t you?”
Her mouth fell open, and she stared a moment. “Uh, I mean, yeah. But that’s something people do alone, not in front of other people.”
I laughed again. This time it sparked a flicker of frustration in her brown doe eyes. “Sweetheart, if wanking in front of me is a stretch, this is going to be a hell of a month for you.”
“I can’t believe I’m doing this. I’ve lost my mind for sure.”
“Do you want to stop?”
“No. Just tell me what to do.” She squared her shoulders and the brave, determined expression on her face sparked a pang of pride in my chest.
“Slide off your jeans.” She immediately popped the button and unzipped her pants. She meticulously folded them and sat them beside her. I should have encouraged her to wildly throw them to the floor, but the general Lilly-ness of her need to keep the room tidy almost made me as hard as seeing her in her charming plain white panties. “Okay, hoodie next.”
She hesitated and blushed. Fuck, my dick was so hard I couldn’t resist dragging my palm across the front of my boxer briefs. Lilly was the demure, sweet girl I’d always known in the body of a siren.
“I…”
“What’s wrong, Lush?”
“I’m not wearing a bra.”
My smile was so broad my cheeks ached. And considering we were on the verge of a magical month of physical intimacy, I felt comfortable enough giving her a glimpse at the space she took up in my brain.
“Lils, you know it won’t be the first time I’ve seen your tits.”
“What? Oh, God, don’t tell me you spied on me or something.” She clutched her arms over her chest as if to hide, ignoring the fact that she had on a thick, navy blue, University of Michigan hoodie.
“I may be filthy but I’m not a creep, Lush. You remember when you came with us to my Uncle Bob’s cottage? You wore that two-piece to the lake, and it was too big on top. You joyfully burst out of the water completely unaware you were topless.”
“Oh, my God! I forgot about that,” she said with a delightful laugh.
“Well, I didn’t. It’s been one of the top five most effective deposits in my spank bank ever since.”
She pursed her lips and crossed her arms in disbelief. “Oh, come on. You never spanked it, thinking about my near non-existent breasts.”
I took a couple of steps closer and sat on the end of the bed. “Lilly, I don’t lie about jerking off. And I’d prefer it if you didn’t insult your sweet little cans. They became the litmus for all other boobs in my life. They’re the crux of why I’m a small tit guy.”
Her hands covered her face and muffled her words. “I have no idea how to respond to that.”
“Don’t. Just take off your top.”
She dropped her hands and our eyes locked. Bravery seemed to well up in her. She peeled off the sweatshirt and bared her perfect breasts. They looked even better than I remembered. The nipples were a delicious dark rose color and were tightly pebbled thanks to the late spring chill in the room and, I hoped, our spicy convo.
“Play with them,” I said.
My heart began to hammer in my chest as her delicate fingers traced her peaks, pinching and tugging. Her eyes slid shut, and a sweet sigh escaped her lips. My mouth dried at the sound and sight of her.
I ran a palm over my aching hard on. I couldn’t contain my low moan as she squirmed and toyed with her small, pert breasts. Her back arched and her breathing sped up. I needed more.
“Take off your panties.” My voice was gravelly and dark with need.
Her eyes opened and locked on mine. Clearly, she sensed that the time for protesting was over. She wordlessly reached down and slid off the prim white underwear.
“Open up,” I said, motioning to her knees.
She let out a big breath and let her legs fall open.
Well, fuck me speechless!
Never in a million years would I have guessed that Lilly waxed her pussy. It was as soft and bare as a ripe peach and likely just as sweet. Her arousal glistened and it took everything in me not to drop my mouth on her for a taste.
“Show me, Lilly. Show me how you make yourself come.”
Her fingers slid down to her mound, gliding between her pussy lips. My delight at how she obeyed my orders without argument was unfathomable. She let out a breath, her mouth puckering like she was blowing on a hot drink. Using both hands, she pulled herself open, unveiling the soft pink insides and pulled back the hood on her clit, exposing the pearly pink hardened nub. Dipping a finger in her wetness, she circled the tight bundle of nerves.
While she may not have been an expert in sex outside of the norm, she was certainly no stranger to her own pleasure—a very encouraging fact. Within a matter of only a couple of minutes she got herself to the precipice, panting, moaning, and writhing on the bed.
Fuck.
I’d fantasized about every single kind of arousing scenario I could fathom with Lilly in it and never could I have imagined something this simple being this incredibly hot. Her cheeks and chest were flushed red, and her eyes were half-lidded and blissed out. Everything in me was desperate to join in the fun, but my self-control won the day.
“Do you like stroking your wet little pussy?” I asked.
She thrilled me by skipping her typical shocked reaction.
“Oh, yes. It’s so good,” she said, breathily.
Fuck.
“Are you gonna come for me, Lilly?”
“Mmm, yes.”
Her moans became faster, and their pitch climbed higher and higher. I hit my breaking point and simply had to be part of all her beautiful pleasure.
“Can I help a little? Just a finger?” I asked, softly.
“Oh, yes. Oh please, Derek. Please.”
Fuck.
Hearing her moan my name was almost the death of me. Scooting closer to her, I ran my palm up her leg until I reached her pussy and unceremoniously slid my finger into her while she stroked her clit.
“Ohhhh. Oh, God!”
Within seconds she was gripping my thrusting finger tightly. I couldn’t bear thinking about how amazing she’d feel around my dick.
“Oh, God, Derek. I’m coming! Oh, God!”
Her body seized as she let out a yip and clamped her thighs together. Her pussy pulsed and squeezed my finger, and I grinned like the cat who ate the canary.
Pulling my hand away, I couldn’t resist meeting her gaze as she came down from her peak and popping my finger in my mouth to taste her sweetness. Her body shivered with an orgasm aftershock.
A muffled buzz interrupted the beautiful sound of her shallow breaths deepening. “Oh shit,” she said, reaching for her neatly folded jeans. Pulling her phone from the pocket, she looked down at it and paled when she recognized the number. “Dammit. It’s Sarah. She texted that she’s on her way home from her date and do I want to come over and watch a movie.”
“Tell her you’re already here. Killing time until she gets home by masturbating in front of her sexy brother.”
Her resulting stare could have frozen Lake Michigan solid.
“I gotta go.” She quickly slipped on her clothes.
Seeing her beautiful body being covered was a tragedy. “Wait, don’t go.”
“Look, even if I figure out a way to spin my presence here, Sarah will figure out something’s up. She’s way too observant.”
After sliding on her sneakers, she was completely dressed and still a little brain scrambled, from the look of her hazy eyes.
“Well, you passed your first lesson. Call me tomorrow and we’ll get cracking on some more adventurous stuff.”
She stared at me curiously.
“You know, after all this, you never kissed me.”
Fuck.
“Do you want me to kiss you?”
Her eyes were soft and vulnerable as she nodded. In an instant, I slid my hands over her cheeks and bent down to press my lips to hers. I couldn’t count the number of times I’d imagined what it would feel like to kiss Lilly. The reality was so much better. Her lips were velvety and wet. The tiny moan she let out against my mouth made me light-headed, and the grip of her arms around my neck made me want to plop her into my truck and drive straight to Vegas for an impromptu wedding. How strange, to kiss someone I already loved.
Far too soon, she pulled away and darted out of the room, calling “Talk to you tomorrow!” over her shoulder.
What the ever-living fuck just happened?