by Rye Hart
She kept things professional, which I admired. But, as the days wore on, part of me yearned for something more than a quick text exchange. Before the arrangement, I actually had enjoyed her company. She made me laugh more than anyone I'd ever known. I was so used to submissive women letting me call all the shots, but Casey was different. She didn't take shit from anyone, me included.
Part of me fantasized what sex with her would be like. I was sure we'd both fight for dominance, but in the end, I'd win. I'd tame her in the bedroom, or at least I had fun imagining what it would be like. Since we'd be doing the deed on a schedule, it wasn't like we could spontaneously fall into each other's arms. I hoped it wouldn't be awkward, but this was a first for me.
That morning, I'd texted her and was waiting for a response. It took longer than usual, but I tried not to worry. Figured she was just busy doing whatever it was she did. Come to think of it, I had no idea what she did for fun, or what her family life was like. I knew so little about her.
She was mysterious and beautiful and amazing, and exactly what I didn't need in that moment. I tried to focus on work, but found myself checking my phone every few minutes, eagerly waiting for a reply. Finally, when my phone buzzed, I snatched it up off my desk in a hurry and read the message.
I read it and re-read it several times over, and it still took me a long time to believe what it said.
It's time. I'm ovulating, so we should get together soon.
I stared at her message, my hands trembling. It was time. Not knowing for sure how long we had, I grabbed my jacket and started texting her as I walked out of my office.
I was on my phone, not watching where I was going, and that was a mistake. Adam and I nearly collided, though I suspected he'd done it on purpose. “Where you off to, Malcolm?” he asked. “A little early for lunch, don't you think?”
Lunch. Yeah, not quite. Food was the last thing on my mind. Not like I wanted to tell him I was headed out for some afternoon delight, it was none of his business.
“I have a meeting,” I said.
“A meeting?” he asked, looking perplexed. “Funny, I didn't see anything on your schedule. I was just coming by to talk about the marketing plan you put together. I had a few ideas I wanted you to consider.”
“Last minute, sorry,” I said as I pushed past Adam and yelled back at him, “Talk to Alyssa and have her schedule you in for tomorrow, maybe?”
I had no idea how long I'd be with Casey. Better clear off the rest of my schedule for today. With a quick word to my assistant, Alyssa, I was good to go. I didn't want to do the deed and leave, that seemed like a dick move. Then again, she might find it awkward to cuddle afterward.
I had absolutely no idea what I was doing, and I had a feeling Casey was going to be just as nervous as me. Probably more so. After all, I wasn't the one getting pregnant.
I'd texted Casey the address of a hotel. Figured neutral ground would be better than either of our places. Besides, my mom was home most of the day, and the last thing I needed was her prying eyes and ears.
Moms are natural boner killers, it goes without saying. Not knowing Casey's familial situation, I figured I shouldn't make assumptions. Her parents could be home too, for all I knew. I thought she said she lived with them, but I couldn't be sure. Hell, I had the condo, but Danielle walking in on us would certainly ruin the mood too. Although, it might be worth it, just to see the look on her face.
A hotel was the best option, and I just prayed Casey didn't feel like a prostitute. That was the last thing I wanted. I owed her, big time, for everything she was doing, and I didn't think she'd ever understand just how much it all meant to me.
Casey texted me back as I climbed into my car. A simple one letter answer, K. She then followed it up with another text. I'm heading over there now.
~ooo000ooo~
I'll admit, I could have done better. The Hilton wasn't exactly the type of place I typically stay at, but it was close by and would have to do. It wasn't the greatest, but it wasn't like we were on a vacation get away. It was literally just for a few hours. Maybe less, depending on how everything went down.
I got there before Casey and sent her a text with the room number. My stomach in knots, I paced the room, waiting for what felt like an eternity before there was a knock on the door. I pulled open the door, and there she stood. My heart stopped for a moment as we saw each other for the first time in days.
She wore a sundress, pale pink and white. It illuminated her features and brought out the warmth in her skin that I hadn't noticed before. Her hair was loose, falling over her shoulders, around the curve of her chin and down her back and over her chest.
We locked eyes, and she smiled at me. I couldn't help but smile back at her, and all the anxiety from earlier vanished away. I could do this. She was a beautiful woman, and all we had to do was have sex. Sex with her was going to be easy, I realized, as she entered the room. I tried not to stare at her ass but failed. The dress highlighted her small waist and the curves of her hips and bottom delightfully.
“Well, hello there,” I said.
She turned and looked up at me through thick, black lashes, her hazel eyes sparkling.
“Hey, Malcolm,” she said. “Good to see you.”
“Good to see you too,” I said.
Any fear of performance anxiety went right out the window, as blood rushed to the lower part of my body. I was growing hard simply by looking into her eyes. She looked away from me, color rising in her cheeks.
“You look really good,” I said.
“Thanks. I tried to look nice for you,” she said.
She bit her lip, but still wouldn't look up at me. I yearned to see into her eyes, so I touched her chin softly, turning her face up toward me. Her skin was so smooth to my touch, and her hair tickled my hand as it brushed against my skin.
“You're beautiful.” I said the words before I could stop myself.
Once they were out though, I didn't regret it. Seeing her face light up was worth it. If I could somehow make this whole process any less awkward for her, that was what I was going to do. Without going overboard, of course. Wouldn't want to give either of us the wrong idea.
“So, this is it?” she said, letting out a deep breath. “We're really doing it.”
I wasn't sure if she meant the sex or getting pregnant, and I didn't get a chance to ask. She turned, pulling her hair away from her back.
“Do you mind unzipping me?”
I reached for the zipper, but it didn't feel right. It didn't feel right at all. I noticed she was trembling, just slightly. Instead of unzipping the dress, I massaged her shoulders. She let out a soft sigh as I kneaded the muscles in her neck and back, feeling the tension melt away under my hands.
She glanced back at me, relief in her eyes.
“We don't have to rush this,” I said. “I want you to be comfortable.”
I want you to want this, is what I really wanted to say. If she didn't want to be with me, there was no way I could fuck her. It would feel like I was taking advantage of her, and that went against everything I stood for. If she decided she didn't want to sleep with me, I'd have to understand and find someone else.
Casey turned around to face me, my hands falling at my sides. She reached out and took one of them into her hands. They were soft, warm, and so smooth.
“You make me feel comfortable, Malcolm,” she said. “I forgot, for a moment, what it was like to be in the same room with you, but now that I'm here – this all feels so natural.”
“Good,” I said, squeezing her hand. “Because if at any time you don't want to go through with this, just say the word.”
She chuckled. “There's no way I'm backing out, Malcolm,” she said. “You don't have to worry about that.”
She stood on her tip-toes and I leaned forward, her hair brushing against my cheek as our lips met. A shockwave coursed through my body, a warmth spread across my skin and down to my groin as our lips brushed against one another's. Casey pull
ed back and stared deep into my eyes.
“I know we can't get too attached to one another,” she sighed. “But I don't want this to be awkward either.”
“I agree,” I said, stroking her cheek tenderly. “I want you to enjoy this.”
“And I want you to enjoy it too,” she said as she leaned into my touch. “There's just one thing I think you should know – ”
“What is it?”
She closed her eyes and rested into my touch. “I'm – well – I'm a virgin.”
My entire body froze, and I felt entirely rooted to my spot. As if she could send the tension in my body, Casey opened her eyes, concern written across her beautiful face.
“Is that going to be a problem?” she asked.
“I just – well, I really don't know how I feel about being your first, Casey. Especially under these circumstances,” I said. “Your first time should be special, not just a babymaking activity.”
She moved her head just enough so that my fingers rested against her lips. She kissed them gently before speaking.
“I have no doubt we can make this special, Malcolm. I need to do this,” she said. I pulled my hand away, but she grabbed it back. “I want this.”
She kissed me again, her lips pressing against mine and took the words right out of my mouth. Her body pressed into mine as our tongues met, setting off explosions of sensation inside of me.
“I want this, Malcolm,” she repeated, her lips moving against mine. “Please, don't deny me. Let me have your baby.”
How could I resist a woman literally begging me to fuck her, to have my child? I couldn't. My body ached with a need I couldn't resist. I picked her up in my arms, lifting her feet off the floor, and carried her over to the bed. I laid her down, gently, and fell on top of her. We continued kissing as I explored her body and she explored mine. Her tiny hands removed my suit jacket, letting it slide to the floor, before she went for my buttons.
My cock grew harder, aching as it fought against the confines of my slacks, pressing into Casey's belly. My shirt fell to the ground, and Casey raked her nails across my flesh.
“Yes, yes, Malcolm,” she groaned, arching her back up toward me.
It was her first time, and I didn't want to hurt her. I wanted her to feel good. To truly enjoy herself and not regret me being her first. I moved down the length of Casey's body as she stared up at me, a confused look on her face.
“What are you doing?” she asked.
I didn't answer her. Not with words at least. I lifted her dress up, exposing her thighs, and dotted soft, gentle kisses along her skin. She groaned, her body shuddering as I inched closer to her panties. From between her legs, I could smell her. It was the delicious, musky scent of a woman who was turned on.
She wasn't lying when she'd said she wanted this, I thought to myself.
I slid the panties aside and dove into the freshly shaved pussy, my tongue lapping at her clit. Casey jumped and let out a soft giggle of surprise, but then her hands found the back of my head and she was groaning as I went down on her.
I sucked and licked and tasted her wetness, slipping a tongue inside of her warmth. There's nothing better than making a woman orgasm with your mouth. Feeling her body tense and writhe underneath you, the muscles of her pussy spasming around your tongue was one of my favorite things. I loved the taste of it, the knowledge that I was giving pleasure to someone.
Casey's nails dug into the back of my head, her entire body tensed up as every muscle contracted and released while I worked on her with my mouth. I knew she was close and kept eating her out until she screamed.
“Oh God, Oh God, I'm – ”
The rest of the sentence was incomprehensible as she spasmed wildly, her thighs tightening around me as she came. After the last throes of her orgasm, Casey collapsed flat onto the bed, her entire body limp. She looked down at me, her eyes half closed and a crooked smile on her face.
“That was amazing,” she whimpered. “But why –”
I slipped her panties down and off her body as I answered, “It's your first time, Casey,” I said. “I want you to enjoy it. And in order to enjoy it, you need to be relaxed. What better way to relax you than warming you up with an orgasm first?”
She smiled wider at me as I tossed her panties on the floor beside us. I reached for my belt, and Casey sat up, helping me unzip my pants. Her hands were still shaking slightly, as she slipped my pants down, exposing my cock.
I watched her face carefully, as her eyes grew wide and her mouth fell open into a perfect “O”. She stared down at my member, then up at me with absolute lust in her eyes. I'm fairly well-endowed – another reason to make sure Casey was ready for me.
As much as people like to fantasize about sex with virgins, truthfully, it usually sucked for both parties involved. Unless you were into hurting your partner, that was. And I wasn't. Not at all. I pulled at the sundress, forgetting about the zipper in the back, and lifted it up and over her head. Something ripped as I yanked it off, but neither of us seemed to care at that moment. The tip of my dick glistened with pre-cum, and my balls ached from the semen building up inside of me.
While I hadn't told Casey about it, according to our fertility specialist, I wasn't allowed to masturbate for days to make sure my sperm count was high enough to hopefully get the job done the first try.
Not that I'd complain about future tries, but time was of the essence.
Casey laid back down on the bed, naked except for a black, lacy bra that held her D-cups. I fell down, on top of her, dotting kisses along the cleavage as she wrapped herself around me. I adjusted her body, so I could reach the hooks in the back, removing the bra and tossing it to the side.
Her nipples stood out from her breasts, perky and pink, and I kissed her right one gently. Casey whimpered, her eyes fluttering closed as I took it between my lips and sucked, keeping my eyes on her face as I did so.
“That feels so good,” she moaned.
“Good,” I said. “I want you to feel good, Casey.”
I pressed myself into her, the tip of my cock brushing against her clit. So close, so very close. Just one thrust and I'd be buried inside of her warm, wet pussy. As if Casey could read my mind, she looked into my eyes and smiled.
She raised her body upward, and tried move things along, but I slipped, rubbing against her instead. It was just a taste of her warmth, of her wetness, but it was enough.
I had to have her.
I steadied myself on my arms, hovering just above her, and looked deep into her eyes as I took hold of my dick with one hand. I didn't need to ask her if she was ready or if she was sure, her body told me that she was. She wrapped her legs around me and I slipped, just the tip, between her moist lips.
Casey bit her lip.
“Does it hurt?”
“No,” she said.
I feared she might be lying. She pushed her body upward, taking more of me inside of her. I spread her open, stretched her farther, and that was the point of no return for me. I thrust myself into her once more, the tightness of her closing around me. My head fell forward as I was sheathed inside of her.
Casey gasped, her legs tightening around me and her nails dug into my back. I looked up, into her eyes, my cock buried inside of her. I kissed her sweet lips, convulsing with pleasure from the muscles squeezing me down below.
God, she felt so good. So tight. So warm.
Slowly, we started moving together. Our bodies worked in unison, as we rocked back and forth once she was used to me being inside of her. Her eyes were wide, her groans growing louder as I moved inside of her.
Maybe it had hurt a bit in the beginning, maybe not. But, we were very clearly past that. Her wetness helped ease me in and out of her, and she held onto me for dear life as we made love.
I knew I couldn't hold out for long though. I could feel that my orgasm was already building up inside of me, preparing for me to explode. Going without sex or masturbation had weakened my endurance and knowing that I wa
s about to shoot my seed inside her, aiming to impregnate her, only made me weaker.
Still, I wanted to make her orgasm again too, I wanted to feel her thrash wildly beneath me, cry out in sheer ecstasy. Gritting my teeth, I held out for as long as I could. Casey's face was a mask of pure bliss, and she cried out.
“Oh, Malcolm! Yes!”
Just like that, I felt her pussy squeeze down around me hard, tightening her even more than before. It was as if her body was begging for me to explode inside of her. That was it, that was all it took. One look down at her, and I groaned, feeling my cock pulse and throb as I spilled my load inside of her. Streams of hot cum shot out of me and into her, filling her up, as we rode out the waves of pleasure for as long as humanly possible.
When every lost drop of my seed was nestled inside of her, I stayed there, on top of her, my cock still sheathed deep within her, was we savored the moment. Never before had I fucked with the intention of getting a woman pregnant.
This was entirely new to me – and I couldn't deny that part of me was even more turned on now. Knowing that my sperm was moving through her body, hopefully reaching an egg and putting my baby inside of her womb. There was something magical, something powerful, and profound about that.
I looked down into Casey's beautiful, hazel eyes, and pushed her hair back from her face. I dotted kisses along her jawline and neck, then moved to her mouth. She kissed me back, and even though I'd just unloaded inside of her, I felt myself growing hard again.
I pulled away from the kiss and fell down onto the bed beside her. She stayed on her back, staring at the ceiling, a near dazed look in her eyes. Maybe she remained in shock over the fact that we'd just had sex, or maybe she wasn't sure what to say. I couldn't be sure. But she just laid there, staring up at the ceiling, a look somewhere between disbelief and rapture on her face.
“Come here,” I said, my voice soft as I urged her to curl up beside me.