Chapter 28: Learning Together

I followed Olivia into her bedroom, kissing her feverishly. My lips danced over hers, as I held her face between my hands. Olivia whimpered softly, walking backward toward the bed eagerly.

On one hand it was endearing that she was so excited for this, on the other hand I wanted to slow it down and savour these moments.

I sat down next to her on the bed, and before long, she drew one thigh over my lap and was straddling me. We both awkwardly tried to gather her skirts so she wasn’t kneeling on them. Her intentions were clear, and while I continued kissing her passionately, I carefully laid back, bringing her with me.

I ran my hands up her hips, my hands lost in the flowing fabric of her skirt. Her hands were in my hair, seeking more contact between us.

I focused on that plump bottom lip that caught my attention and frustrated me so often, pulling it gently between my lips.

Her answering moan made me almost come unglued. My hands moved up her body and into her hair.

She broke the kiss and sat up, reaching into her hair. My hands landed on her hips, waiting. She released her hair, sending the chocolate ringlets springing around her face.

“Better?” She smiled.

“Much.” I breathed, sitting up and bringing her lips back to mine. My hands explored her hair carefully.

Olivia’s tiny hands laid gently on my chest, not sure where to begin or how to start. I could no longer control myself, I rolled her gently onto her back, settling between her thighs, my hands wandering up the silky, smooth plains of those legs. My right hand found it’s way beneath the skirt, while my lips traveled down her throat.

Her sexy, heavy breathing was right next to my ear as her whole body arched against mine. “Oh, Isaac.” She breathed.

I moaned at her shoulder uncontrollably.

Just before my fingers reached her hip beneath her skirt, she stopped. “Isaac, wait. Please?” She breathed.

I withdrew my hand immediately, worried she might want to stop. I’d pushed her too far and she was rejecting this whole notion.

I swallowed. “I’m sorry, Liv.” I pushed myself up onto my hands. “We can stop.”

“No.” She shook her head, her chest heaving slightly from our efforts. “I… can you just give me a moment… to change into something more comfortable? Please?”

I nodded, relief flooding over me. She wanted to continue. “Yeah, of course.”

“Just… two minutes. I’ll be right back.” She said, smiling softly.

“Yeah, of course.” I answered, swallowing roughly. This could only mean one thing. She wasn’t sure. She was going to collect herself and mull over the decision to continue. I wasn’t going to force her or trick her into anything she didn’t want. If she decided she couldn’t do this, then that was it. It was her decision alone. And no matter how much I wanted it, I had no choice.

She shyly kissed me and hurried from the room.

Once Olivia was out of sight, I removed my suit jacket, draping it over her desk chair. I yanked my tie free, and untucked my shirt. I sat anxiously on the edge of Olivia’s bed, trying to smooth my hair down a little. It was blatantly clear that Olivia and I wanted the same thing. It was going to happen tonight.

I was the one with the experience in this matter so I knew I had to be slow and careful with her. I had to make this last, and enjoyable for the both of us. This wasn’t like most of the previous times I’d had sex; it wasn’t a desperate, selfish race to both get off.

I checked my pocket awkwardly, to be sure the condoms I had stashed there were still where I had left them. It would be beyond unfortunate if they had fallen out.

Olivia seemed to be taking a long time. I began to panic. What if she was having second thoughts?

I ran my fingers through my ponytail awkwardly.

I plopped down on the edge of her bed exhaling slowly. I glanced around her room, at the pictures, movie stubs, post its, hand written notes she had adorning one wall.

“Hi.” Olivia said suddenly.

“Hey.” I answered, before I turned. I turned and felt my jaw practically hit the floor. Olivia was wearing a deep navy blue outfit. The push up bra was decorated with beads and lace. It perfectly accentuated her pale, creamy skin. Her hair hung in perfect ringlets around her shoulders. My eyes roamed down to the silky ruffled panties in a matching blue. She had on translucent black thigh-highs and a staggering pair of black heels.

I swallowed thickly. “Holy shit, you look hot.”

Olivia laughed softly, glancing down to hide her blush. “Do I? Because I feel silly.”

“Definitely not silly.” I stood and moved toward her. I lightly stroked her hair back behind her ear and when her eyes met mine again, I kissed her.

Tentatively she was trying to inch my dress shirt up. I hastily jerked my shirt over my head, pulling her close again.

Before long, I laid her on the bed, with her head on the pillows. I moved on top of her. I moved between her parted thighs, and just the feeling of being pressed against her was sheer heaven.

Her shaking fingers tried to unlatch my belt. I kicked off my dress pants and was down to my boxers in seconds.

I kissed a slow, deliberate trail down her throat to her shoulder.

“Isaac…” She whispered softly.

“Hmm?” I murmured, buried in the sweet scent of her skin.

“Go easy on me? Please?” She whispered. “I’ve never done this before.” She breathed.

“I know. I will.” I replied.

I pulled the sheet over us both, my lips returning to hers. I made up my mind to make this as easy on her as I could.

I placed several short kisses on her lips. “If at any time you want to stop, we can. We’ll stop the second you say the word okay?” I lightly stroked her cheek with my thumb.

Olivia nodded. “I want to.”

“Okay.” I kissed Olivia with passion, throwing everything I had into it. I licked her lips and our mouths opened, in savage hungry kisses. I released her, her chest heaving against mine. I slowly savored her skin, finding any sensitive spots along her neck and collar.

I lapped kisses down her chest to the swell of her breasts, lightly running my tongue across the plump pale flesh. I lightly cupped her breast, causing her to whimper softly.

I smiled to myself and decided that for now I could make due with feasting on her supple, soft flesh. She arched against me, reaching behind her to unclasp her bra and free her breasts for my mouth to explore fully.

I caught her hands and pinned them at her sides. “Not yet.” I warned lightly.

She sunk her teeth into her lip and nodded trustingly.

I explored her soft, flat stomach with my hands, wandering over her hips, down her thighs, and lightly brushing her breasts. Her heart was pounding hard, and she was breathing heavy.

I decided I had tortured her quite enough, finding it hard to withstand the torture myself. I kissed and lapped my way down her smooth belly, smelling and feeling her arousal. She stiffened slightly drawing in a deep breath and arching her back slightly.

I could see the effect I was having on her, but instead of worshiping every inch of her skin, I lightly ran my hands beneath the silky fabric of her panties. I felt the wetness, I waited for her to stop me, but she simply watched silently, her teeth still working her lip.

I slipped her panties down her legs, leaving the sexy stockings on.

I moved back up until my face was level with her waist. “Keep going?” I asked permission.

She nodded. “Please.” She breathed, breathlessly.

“Okay. Relax.” I lightly stroked her hip. I slipped beneath the cotton sheet, exploring the unbearably sexy fresh bikini wax with my lips. Her knees bent, and I carefully urged one foot nearer to her perfect ass.

I wanted more than anything to explore her, to find every little motion that made her whimper. My hot breath moved over her wetness causing her to shiver slightly.

I kissed her center, exploring her lips before carefully delving deeper. I placed my hands on her thighs, holding her still and open.

My hands pushed her further apart, her body tensed, but as soon as my tongue slid between her hot, silky folds, she gasped in pleasure. She whimpered, writhing beneath me, her breathing was loud and labored, panting as I licked every nook I could find. I lapped up her juices, dipping my tongue in and out of her.

I knew there wasn’t much I could do wrong, but again I knew that Olivia meant a lot to me, and I was determined to make this a night she remembered. My tongue moved deeper, and her hips bucked wildly. I held her steady somewhat forcefully.

I decided I’d tortured her enough, she deserved the greatest release I could give her. I found her clit, gently nursing it between my lips.

She gasped sharply, the sheets below her fisted in her hand. “Oh, god, Isaac!” She gasped.

She was making such sweet, musical sounds, I sucked harder. Her hands found their way into my hair, and she tugged lightly. “Oh, I can’t! I… I’m going to… oh, god!” She shrieked and her whole body began to spasm below me.

I moaned, causing the vibration that pushed her over the edge. The sound of her crying my name as she climaxed was the sweetest sound I’d ever heard.

I finished with a few more teasing licks against her trembling body and climbed back up her.

She tossed her head to the side, gasping hard. Her chest was heaving, causing her full breasts to strain against the dark blue bra.

I reached out and caught her cheek, turning her face back to mine. I kissed her so deeply, she whimpered at the taste of herself on my lips.

I kneaded her breast in my hand, my thumb raking across her nipple. She whimpered again.

I moved on top of her, pressing my raging erection against her already tender center.

“Oh, Ike. Please, now.” She whispered against my lips.

I lowered my lips to her throat. “Not yet.” I warned in her ear.

I reached around her and released the clasp on her bra, freeing her delicious full breasts to my touch.

I moaned, cupping her breast gently. I moved my thumb across her nipple, feeling it harden.

I smirked and moved my mouth around it.

She gasped, throwing her head back and arching to my mouth. I gently squeezed the perfect mound of her breast, I swirled my tongue around her nipple, and her hand moved into my hair, clasping my lips there.
I slowly slid my hand down her smooth stomach, sliding my hand between her thighs. Her legs instantly opened wide for me. I could feel her wetness already pooling there. I readied two fingers and lightly slipped them inside.

She cried out, and at first I was afraid I’d hurt her, but she moaned and whimpered.

My fingers moved slowly as my mouth and tongue took turns on her nipples.

Her head tossed from side to side as I slowly moved my fingers in and out, pumping at a slow, even pace.

I glanced up at her, seeing her swallow and struggle to watch my ministrations. “Faster.” She panted. “Oh, Isaac, faster. Please…” She whimpered.

I wanted to give her everything, I wanted to make her feel amazing. I began pumping my fingers inside her faster, speeding up gradually. I stroked her clit with my thumb, while I suckled on her nipples. She was lifting her hips in gentle thrusts, not sure what to expect. She arched against me, and when I felt her get close, she tossed her head back and cried out my name louder than the last time. Her second orgasm rocked her tiny body hard.

She dropped back against the bed, panting hard.

I lightly stroked her hip. “Do you want a break, Liv?” I asked. “Slow down for a bit?”

She shook her head quickly. “No! I want you!” She panted. “Now.”

“Okay.” I pursed my lips, trying to think of how to continue. I wanted the easiest route, and the less painful for her.

She already pushed me onto my back, climbing onto my lap. She was working off my boxers, and when my erection sprang free, she gasped softly.

“Are you having second thoughts?” I worried.

“No… I just… I’m not sure how it’ll all fit.” She admitted.

I chuckled. “We’ll give it a shot.” My ego was the second thing painfully swollen in the room. Now that I was thinking about it, my erection was growing painful.

I kicked off my boxers and reached for a condom from the nightstand.

“I’m sorry. I feel so unprepared.” She admitted. “I have no idea how to do this.”

“It’s alright. We’ll learn… first things first, though.” I held up the condom.

“You’ll have to show me that too.” She admitted.

“Yeah, sure.” I showed her how to put the condom on, her tiny, tentative fingers following mine. She gave a small smile.

“Are you ready?” I asked, eagerly. I was throbbing, I needed release.

She nodded, sitting up onto her knees.

“Here.” I placed my hands on her hips, urging her over me. She prepared to sink down fast, but I stopped her, grinning at her eagerness.

“Wait, wait, Liv. Not so fast… this part we have to go slow.”

“Right.” She nodded.

I held her hip. “Ready to try?”

She nodded eagerly.

“Let me know…”

“I will.” She panted.

“Okay.” I inched her down slowly, sliding into her carefully.

She gasped and stiffened.

I stopped, waiting, and studying her face. “Are you okay? Does it hurt?”

She shook her head, ”I just… wasn’t expecting it.”

“Do you want to stop?”

“No!” Her eyes grew wide.

“Okay… tell me when.”

“When.” She smiled.

I moved her down slowly, sliding into her easily, another inch or so.

She gasped and I stopped. “Oh!”

“I’m sorry. We can stop!” I began.

“No, no. It’s fine.” She insisted. “It only hurts a little.”

“Liv, if-“

“No, it’s okay. Please, I want this.” She insisted.


Before I could do anything else, she sank down the rest of the way. She gasped sharply, crying out painfully. Her fingernails dug into my skin.

“Olivia-“ I began.

She tossed her head back. “Oh, god!”

I chuckled. “You’re okay? It doesn’t hurt?”

“No. It feels…” She sighed. “Good, actually. Really, really good.”

Her chest was heaving again, and her eyes closed. She pursed her lips to suppress a moan.

I smirked, pressing a kiss to her shoulder. Her hands moved into my pony-tail, her lips at my ear. “I’m ready. Please. I want it.” She was trying to reassure me, but it came out as a sexy coo.

I smirked, rocking her hips, pulling her toward me, and backward.

Her head rolled back onto her shoulders, and I grinned, latching my mouth over her breast again.

“Oh!” She cried out, “Oh, yes. Ike!” She squealed lightly.

I began pushing into her a little harder, her breath quickening. My own desire began to ache. I wanted to take it slow, but it was killing me. For so long I’d wanted this; desperate for this moment.

At this rate I was going to finish before she was.

“Liv, spread… spread your legs, just a little more…” I groaned, pushing up into her. I moved my hands into her hair. “Yeah, just like that, baby.” I kissed her deeply.

She moaned against my lips.

I couldn’t help it any longer. I had to have release. I rolled her onto her back, letting her loop her legs around my waist. I pumped in and out of her, daring to go harder and faster with each thrust. She panted hard, her heart beating faster and faster. Her head tossed from side to side.

I caught her hands, pushing them back onto the bed and interlacing my fingers with hers.

She screamed this time, throwing caution to the wind and closing her eyes as her third orgasm ripped through her. Mine came seconds later.

It was by far the sweetest release I’d ever had.

While I waited for her trembling to stop, I littered her face with kisses.

Soon after, we fell asleep wrapped in each other’s arms, and twisted in her sheets.