Page 27 of Arrogant Matchmaker


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I reach for my discarded pants and pull a condom from my wallet. I push off my boxers and roll on the condom. I kneel between her legs, my cock looking huge compared to her.

“You sure about this?”

She nods. “Yes. I’ve never been more sure.”

I take her for her word and notch my cock at her entrance. I slowly push inside, determined to make this good for her. I push in inch by inch, retreating and thrusting, stretching her until she’s taking every inch.

“Fuck, angel, you’re so tight…”

Olive makes some kind of inarticulate noise that I take for encouragement because those bright blue eyes of hers are heavy-lidded and dilated from pleasure. If I had any doubts, those are blown away when she wraps her legs around me and starts moving with me.

“Oh God…” she moans at the tight fit as she takes me even deeper. I freeze inside her, giving her time to adjust to the new angle and depth. Olive’s nails dig into my back as she wriggles beneath me. “Move… please… don’t stop…”

I crush my lips to hers, owning her mouth as I pull my hips back then thrust back inside. Over and over, I move inside her tight sheathe. Olive comes alive under me. She follows my lead, rolling her hips with my movements. Her fingernails dig into me, a silent threat for if I decide to slow down or stop. What she doesn’t realize is that we are beyond that now. There’s no stopping. No pausing. No holding back.

My reservations from just last night are gone. Yes, the reality of her getting too attached is still there, but I can’t find the worry I’ve been carrying around since I found out that she’s a virgin. I don’t do relationships and taking the virginity of a woman Olive’s age usually signifies a relationship or at the least the promise of one.

Those thoughts don’t seem nearly as suffocating as they once did. Some insane part of me likes the idea of keeping Olive all to myself and not just for sex. I like her. She’s funny and sweet and smart. She’s quick-witted and independent—everything I would want in a match. Rita would just love knowing that, wouldn’t she?

I push the thoughts away, wanting to stay in this moment with Olive. Wanting to focus on the hot squeeze of her cunt around my cock, the way her hips roll underneath mine. My balls draw up, and my spine tingles. I’m on the verge of release, but I refuse to go without her. Olive will always get hers first. Always.

I slip my thumb between her folds, finding her clit. I stroke her with purpose until she’s writhing underneath me, and her pussy is squeezing me in a vise.

“I’m gonna come,” Olive moans. “So close…”

“That’s it, angel,” I say, my voice rough with lust. “Come all over my cock.”

“Yesssss…” she hisses.

Her pussy locks down on me, and her back arches as she comes for me. The last of my sanity slips away, and I start to pound into her virgin-tight pussy. My cock shuttling in and out of her like it owns her because it fucking does.

I throw my head back and roar as my orgasm explodes through me. My cock jerks, filling the condom. I have a moment of regret that I’m not filling her bare cunt, but I shake that crazy thought away. I’ve never even considered sex without a condom before. Why the fuck do I have the desire to do so with a woman I’ve only known for a short time… a virgin, nonetheless.

Olive collapses to the bed bringing me out of my insane thoughts. She’s flushed and panting for breath. “That was… wow,” she says with a little giggle.

I shake my head, chuckling at her cuteness. I lean down and kiss her nose, then quickly dispose of the condom. I crawl back into bed and pull her into my arms. Unlike last night, she quickly melts against me, all the awkwardness completely gone. I hold her as we both catch our breath, loving the feel of her in my arms.

She’s quiet. Maybe too quiet. I can’t help but wonder what she’s thinking about, but I won’t ask. I’m not sure I want to knowthe answers to what she’s got on her mind. My own thoughts are enough to make me uncomfortable. I’m not having ‘just got laid’ thoughts. I’m having ‘just took the virginity of a woman I really like and might want more than just that’ thoughts.

I’m not sure how long we are wrapped up in each other, but I realize it’s getting late, and it’s probably past time for me to get to the office.

“I need to get to the office,” I say, breaking the silence.

She rests her chin on my chest and looks up at me. “Do you have to?”

Regret burns in my gut because I don’t want to go. For the first time since I started my company, I would rather play hooky than go into the office. That’s how far past my comfort zone I’ve fallen. It’s good for the ego that she doesn’t want me to leave.

I pull her up off the bed and lead her to the bathroom. Just because I need to leave doesn’t mean I have to shower alone. The temptation of Olive wet and soapy is almost too much to resist, but somehow, I manage. We wash each other, taking our time touching and exploring but no more than that.

“If I didn’t have to work, I would drag you right back to bed and dirty you up again,” I growl as she covers her sexy body with a towel.

“You’re the boss…” she says, trailing off.

I let out a groan. “Yes, but I’m closing a huge deal. I can’t take off today. I wish I could, angel. I would like nothing more than to stay in bed with you all day.”

What the fuck am I even saying? A woman over work? Who am I? This is all Rita’s fault. I should be mad at the changes in my desire to spend all day every day at the office, but when I see the broad smile on Olive’s face at my declaration, I can’t be upset.

She walks me to the door and kisses me before I leave. Not just a sweet little peck, but a kiss full of the promise of naughtythings to come. We don’t make plans on when we will see each other again, but my newfound addiction to a woman named Olive means I’ll be calling her if she doesn’t call me first.