tagFirst Time"Oh, Jack..."

"Oh, Jack..."

byCaptainPrice626©

Hello, reader. Please note that this is my first story submitted to the site, though not the first erotic fiction I have ever written. Any constructive criticism is welcome, because I am not presenting this work as perfect. It is for entertainment purposes and a hobby that I would like to get into. Happy reading, and please let me know what you think.



"So, do you want to make a handout of the main points of the movie, or make a list of questions for the class to answer?" my partner Allison asked.

"Well, he said we should involve the class a little more. We'd better go the question route."

My friend Allison and I had been assigned a presentation for our history class, and were meeting in the computer lab at school to work on it. We weren't getting anywhere. One guy was listening to his iPod and the volume was so loud WE could hear the lyrics. Another girl over in the corner was talking to her boyfriend on the phone, and was apparently unhappy with him and didn't care who knew it. There was also a nerdy guy at the computer beside me, and he wasn't even doing anything school-related. He was looking at a plot synopsis for some kind of weird-looking anime. But at least he was being quiet.

"Hey, let's go back to my dorm," Allison suggested. "We'll be more relaxed there, and we'll be able to think better."

"Yeah, that sounds good. I'm thirsty." We picked up all our stuff and began walking back to her room.

While we're walking, let me introduce Allison and myself. I'm Jack, and I'm 22 years old and in my final year of college. I'm not a stud, I'll admit, but there wasn't a lot of competition at my school for female attention. I'm about 6'2" with short, dark brown hair.

Allison is my friend whom I had met years before at freshman orientation. She's very pretty, with a kind of pale complexion, brown hair with blonde highlights, and beautiful blue eyes. Her figure was perfect: curves in all the right places. We were both from in town, and so we kind of hit it off. At first I thought that we would start dating, but it turned out she had a boyfriend already. Just my luck. So we have continued our awkward friendship ever since because even though I wanted more, that was no reason not to be friends with a nice girl. Enter present day.

It was a rather hot day in April, and I had (like usual) let Allison walk ahead of me so that I could 'spectate'. She was wearing a blue tee shirt with our school's name, a denim skirt, and flip flops. Most guys go for the tits, but I'm more of a legs kind of guy, and Allison had amazing legs right down to her pink toenails.

I dropped out of my reverie just in time; we were back at her place. She unlocked the door and we went into her room. Her roommate wasn't there, apparently. Allison sat down, kicked her shoes off, and tucked her feet underneath her. She looked up at me with those sparkling eyes and asked me if I was ready.

"Yeah," I said.

"Well sit down, silly!" I sat down opposite her. "You can come closer, I won't bite." She giggled as I hesitantly moved closer.

"Okay, where do you want to start?" I asked. She sighed heavily.

"I don't really know. I only have a little while. Derrick is making me go with him to a basketball game tonight." Remember the boyfriend I told you about? I've met the guy, and he is a douchebag with serious jealousy issues. And probably a small pee pee.

"Making you?" I asked. I noticed that she was no longer as happy as she had seemed moments before.

"Yeah... He's sweet, but sometimes..." She hesitated, and a tear rolled down her cheek. "Sometimes, he tries to make me have sex with him when I tell him no. I've never had sex before, but I want to enjoy it -- not be forced into it." She wiped her face of tears.

I got brave, putting my hand on the soft, bare skin of her leg. "You don't have to do anything you don't want to do. He should be more considerate of how you feel." She looked first at my hand, and then at me. To my surprise, she smiled.

"You're sweet. I've wanted to break up with him for months now, but I don't know how to tell him. I used to be able to deal with it, but here recently it's been really bothering me." She moved closer, and our eyes met. I saw her glance at my lips, and I glanced at hers. We inched closer, our lips almost meeting -- but then she recoiled.

"We can't do this. I don't like him, but I can't cheat on him." I put my hand behind her head and rubbed her neck.

"You can't go on like this if you're unhappy. You're such a sweet, beautiful girl. I've known you for a long time now, and I know that you can do better than him. You deserve better." She smiled.

"I know. You're really sweet, Jack. I've decided what I want."

"Good." I reached for my notebook, thinking that my raging erection would go unhelped. I was wrong. She grabbed my hand. "What are you doing?"

"I want you, Jack."

"What? But we can't..."

"Sssshhh..." She put a finger to my lips. "You know you've always wanted it. And so have I. I've had enough of Derrick's bullshit."

She got onto her hands and knees on the bed, pure animal desire in her eyes. Our lips met softly for a few seconds, we pulled away – and then passion took over. Before I knew it, she was on top of me with her tongue in my mouth. This was it. No more holding back. I grabbed one of her breasts (which I neglected to mention are a luscious C-cup) and she grabbed my cock through my pants. Our tongues danced and intertwined for the first time, what we had both secretly been wanting for years. She sat up, still on top of me, and peeled off her shirt to reveal a black lacy bra.

"Like what you see? My boyfriend bought this set for me – except the matching thong is in my drawer." I hadn't noticed until now, but she was right. She had no panties on, and I could see her neatly shaved pussy. I reached to touch her, and she playfully smacked my hand away. "Not yet. You've gotta be patient." Knowing immediately what she meant, I reached behind her to undo the clasp of her bra.

Her tits were amazing, and she leaned down once again to give me access. I cupped them both in my hands, still hardly able to believe we were doing this. I brought one to my mouth, and flicked my tongue across the nipple a few times. "Oh, Jack... That feels so good. Suck on my titties." I was happy to oblige. As I sucked her nipples, she began to grind her pelvis against mine. My cock was about to rip through my pants at this point, and I knew she could feel it. "God, you're making me wet," she whispered into my ear.

I gently pushed her off of me and laid her on her back. I started at her neck, and kissed slowly all the way down to her bellybutton. Then I undid the button on her skirt, and she tucked her legs up and out of it. Her pussy was so smooth. "You like it when girls shave, I take it," she giggled. I nodded. She rested her feet on my shoulders. "I want you to lick me. You can use fingers too, just not too hard."

I spread her pussy lips and gently licked. Her body tensed up when tongue met skin, and she threw her head back and moaned. I ignored her clit for now, and decided to tease her a little bit. As she moaned and squirmed, I inserted the tip of a finger. Apparently she wasn't expecting this, but continued to moan with pleasure. "Oh, God yes. Lick my clit baby."

"Not yet. I want you to beg me for it." Still slowly moving my finger in and out, I flicked my tongue across her tight little asshole. This drove her crazy, and I had to move my head to keep up with her squirming. I figured I had tortured her enough, and immediately sucked her clit into my mouth. She arched her back, grabbing the back of my head with both hands.

"OH MY GOD......that feels...so good...!" she moaned. I varied intensity, barely touching it with my tongue, and then sucking it back into my mouth. She looked at me, and she was starting to sweat a little. "I want to see what I felt in your pants earlier. Stand up." I stood up, and Allison got on her knees in the floor. She reached up to undo my belt, pulled it off, and unbuttoned my pants. She pulled them down, and her eyes widened. "Wow. It's huge!" Not to brag, but my cock was harder and bigger right now than I had ever remembered it being. Then again, my ex-girlfriend was nowhere near as hot as Allison and never really turned me on.

She lightly stroked my cock with one hand, staring at it like a child would a new toy. That turned me on even more, because I realized that she had probably never given oral before. "Oh gosh, it's getting bigger!" she exclaimed. She continued to stroke it lightly, and then slowly inched her mouth towards it. She licked the tip, which made me shudder. "What's wrong?" she asked.

"Nothing. That just feels really good."

"Oh..." She smiled, pleased and now aware of the control she had over me. She started flicking her tongue across the tip, like I had done to her earlier. She was really enjoying this, knowing that I wanted her to do more. Then, without warning, she took the whole thing into her mouth. She looked up at me with those gorgeous blue eyes and my entire member in her mouth, and I almost came right there. She started to gag a little, and had to breathe for a second.

"It feels...a lot bigger...in my mouth," she said. She took it back into her mouth, and began moving her head in an in-and-out motion.

"Oh my God, Allison...I've fantasized about this so many times since we met." She giggled, and started stroking my cock with her hand again.

"So...what's next?" she said with a grin.

"I...I want to keep going. I've wanted this for so long." I laid down on my back on the bed and she followed, climbing on top of me. For a few minutes, all we could do was look at each other. We both smiled, and she leaned down to kiss me. I ran my hands through her hair as we exchanged passion, and she wrapped her arms around my neck. Then I began to move my hands up and down her smooth back, down to her butt, and then up again. We stopped kissing.

"I want you, Jack. But I also want this to be mutual. Are you sure this is what you want?"

"Yes, Allison. I've wanted this for a very long time, but Derrick always interfered with any thoughts I had of being with you."

"We don't have to worry about him anymore. This is our moment, and I want it to be special."

"Are you ready?"

"Yes. Just go slowly at first." I positioned myself, and she slowly lowered onto my cock. She groaned a little in pain, but kept going little by little. She was so tight and warm, and again I couldn't believe it was finally happening. At last I was all the way inside her. She locked lips with me again, and in between kisses whispered into my ear: "Fuck me hard, Jack."

I grabbed her ass and began pumping in and out of her pussy. She felt so good. She was still in a little bit of pain, but I could tell that the pleasure was far more overbearing. She bit into my shoulder a little, which has always been a turn-on for me. I leaned up and began sucking on one of her nipples while I fucked her.

"You like that cock in your pussy, baby? Yeah?" I said. All she could manage was a "Mmhmm..."

"Here, I'll let you rest a bit. Have you ever heard of a 69?" She rolled off of me onto her side.

"Yes. I've always wanted to try it." She climbed back on top of me, in the reverse direction this time. I don't think I had EVER had a better view of the landscape. She immediately began sucking me off, and I went right to my duty as well. I licked her pussy lips while I used a finger to stimulate her clit. She screamed in muffled pleasure and continued sucking me harder. This went on for a few more minutes, and I noticed that she was convulsing a little. "Oh God, keep licking me! Play with that clitty, baby. I think I'm gonna cum..." I kept licking and grabbed her ass with both hands to pull her down onto my tongue.

"Yeah, cum for me baby." She screamed with pleasure, and in a few seconds her legs tightened around my head as she orgasmed. Out of breath, she flopped onto her back.

"Oh my God, Jack. That was amazing."

"I'm not through with you yet," I said with a wink. "Just lay back and relax." She propped herself up with one elbow, and I lifted her right leg up to my chest and entered her from the front. This time, I was much slower and more deliberate. As I slowly fucked the girl of my dreams, I caressed her smooth leg and brought her foot up to my mouth to suck on her toes.

"Oooh, Jack...that's hot," she moaned. I cupped one of her breasts in my hand and lightly pinched her nipple. "For a moment that's supposed to be romantic, you sure are being a dirty boy," she giggled.

I laughed. "And you look like you're enjoying it, dirty girl." As I pumped slowly in and out of her, a thought occurred to me. It scared and excited me.

"Hey, what if your roommate comes in and sees us?"

"She's such a slut that she'd probably ask to join us."

"And...?" I asked, half jokingly, half serious.

"Aaaaand I'd say hell no. You're mine tonight. But she is kind of cute..." I kissed her foot again and started fucking her a little bit faster.

"And so are you." She blushed a little, which was kind of strange considering what we were doing.

"You know what I want now, Jack? I want you to fuck me hard and cum all over my face." I don't think I could have held it in much longer anyway. I began pumping her as hard as I could, and the bed began to creak. "YES! Fuck me harder! Fuck me harder!" This sent me over the edge. I pulled out of her and moved up to her face. She licked her lips with anticipation and began to stroke my cock again. "Cum for me, baby. Shoot that cum all over me." A few more seconds and I exploded onto her face so hard she had to close her eyes and let me finish. When all was over, she had my cum dripping off of her face and onto her bedspread.

"Fuck..." I said, and now I was the one out of breath. "That was...wow." She got some tissues from her nightstand and cleaned up our mess as best she could. Then we both lay down and held each other. She laid her head on my chest.

"I'm glad we did that, Jack. I feel so liberated now. And..." She looked up at me, and a tear rolled down her cheek. But it was a happy tear. "And...I love you."

"I love you too, Allison. I always have." She smiled, and we kissed not as friends, like before, but as lovers. I slid my tongue into her mouth—

And the door opened.

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