17 and Ready: A Teenage Virgin's Desperate Plea for No Strings Attached Sex

Three more days. That's the thought that kept me going. Three days and I would definitely be losing my virginity. Y'see, I had made a pact with my best friend, Emily, that if neither of us had lost our virginity by our 17th birthdays, we would lose it to each other. Why 17? Don't ask me. It was a pact we made one boring lunch during freshman year. Emily had turned 17 months ago. I, as you've probably guessed, had three more days.
Emily was not making it easy, either. She had always been a major cock-tease, and had stepped up her game recently. She would brush past me, reaching down and grabbing my member as she went. If she dropped something, she would bend at the waist, allowing me a generous view of either her backside or her breasts. Her hips swung as she walked, and she always made a point of walking in front of me.
I suppose I should describe myself and Emily. I'm an average guy; About 5'9", 150 lbs. I had dark brown (almost black) hair, and brown eyes. I wasn't the most attractive but I wasn't unattractive, either. Emily was short and curvy. She might have been 5'3", 125 lbs. She had shiny brown hair and amber eyes. Her slight Asian heritage gave her a nice, warm skin tone. Emily's bust was around a 12 C cup, and her breasts appeared perky. Her ass was wide and round.
Three more days. Today was a hard (no pun intended) day for me. Emily had asked me to get something out of her back pocket earlier, so I copped a feel of her ass. She looked back at me and winked.
"Oh, you naughty boy. You like my ass, huh?" I simply nodded. "I'll remember that." Then she walked away, hips swinging. That night, after school, I got a text from Emily. It was a picture of her ass. She had on pink panties that accentuated her amazing skin. I couldn't help myself; I masturbated to the picture that night.
Two more days. Emily came up to me before school started.
"So, did you like the picture?" She giggled.
"Oh, I sure did. I may have liked it a bit too much." I started to get hard just thinking about the picture. Emily noticed the tent growing in my pants. She gripped it for no more than a second, but I got rock hard.
"Emily," I groaned. "Why do you have to tease me so much?" Emily got an evil glint in her eyes.
"Because I want you as horny as I can get you." And with that statement, she walked away. I gazed at her ass as she left. Damn.
Emily continued to tease me throughout the rest of the day. She dropped things in almost every class, allowing me a whole lot of peeks at her. Whenever she walked past my desk, she would turn so her ass was facing me. It was all I could do to not masturbate in class.
Again, after school, I got a text from Emily. It was a picture of her breasts, this time, held up in a simple purple bra. Unable to help myself once more, I masturbated furiously to the picture.
One more day. Today was Friday. Emily showed up to school in the skimpiest outfit I'd ever seen her wear. She was wearing olive green shorts that barely covered her rear, with a tight, white, low cut t-shirt that displayed her Day-Glo pink bra for all to see. She came up to me before the bell rang. I noticed she was wearing perfume. She leaned in towards my ear and whispered:
"Are you ready for tomorrow? I bought the condoms yesterday, and some really sexy lingerie. You're going to be drooling, I bet." My cock was rock hard in my pants. Emily rubbed her hand against the outline of my erection. She smiled. "Oh, you can expect something later to help take care of this."
Emily was even more of a tease today than yesterday. She made a point of squeezing her arms together so her cleavage was accentuated. Everything she did seemed aimed at turning me on. Damn, was she hot.
Just like the past two nights, I got a text from Emily. This time, though, there were two pictures. One picture was a shot of her sucking on two fingers. The other showed her hand in her panties.
I woke up the next morning to my dad looming over me.
"Listen, son, I know about your little 'pact' with that Emily girl, and here's what I have to say about it..." I waited with bated breath. "I'm so proud of you! You're gonna be banging a hot chick tonight? I can work with that! I'll get your mom outta the house for a few hours tonight, okay?" He grinned and left the room. I felt relieved. I called Emily.
"Hey, Em, my dad's gonna get my mom out of the house tonight for a few hours. He somehow found out about the pact."
"Um, yeah, I told him."
"What?! You told him?!"
"Yes, I did. C'mon, Andrew, think about it. I knew he'd be okay with it. I may or may not have been flirting with him a little, though." I smiled. Emily was notorious for using her looks to get her way.
The day passed slowly. I masturbated whenever I got horny, so I'd last longer tonight. I made sure to clean up my room and have clean sheets, and I showered just before Emily arrived. My parents left about 4:30, which was perfect because Emily was supposed to show up at 5. She'd demanded I dress up for the occasion, so I put on black slacks, a blue shirt, and black tie. I heard a knock at the door. It was 4:59. I walked to the front door and opened it. It was Emily. Before I could say anything, she leaned in and kissed me. Her lips were soft and warm. I felt her tongue enter my mouth and start probing around. I probed back, sending my tongue into her warm mouth. Our tongues wrestled for supremacy, before we finally broke the kiss.
"Wow," I breathed. "That was... amazing." Emily blushed.
"Well, if we're going to do this, we have to do it right." She walked inside. Her outfit consisted of a formfitting sleeveless black dress, 3-inch heels, and a small black purse. We set to work making dinner, which was one of my favorite foods: spaghetti. As Emily browned the meat on the stove, I set the table. I had memorized the silverware placement earlier and set up our utensils without flaw. I poured sparkling grape juice in two tall wineglasses. Then dinner was ready.
As we ate, Emily and I reminisced over times gone by. We'd been friends since 5th grade, back when I was fat and she was a nerd. Now, I was fit (not buff, but fit) and she was a sexy little minx.
Emily had said we were going to do this right. That meant, to me at least, that she would get to orgasm at least once. That was my mission. After dinner, I took her hand and led her to my bedroom. I grabbed her waist and pulled her in for another kiss. She wrapped her arms around my shoulders, and I lowered my hands from her waist to her ass. She pressed herself against me. I felt her breasts squish against my chest, and her pelvis ground against my hardening member. I ran my hands up and down her back, savoring her warmth. I found the zipper on her dress and slowly pulled it down. Emily broke the kiss and placed her forehead against mine. Her breath was warm on my face. Her dress slipped from her shoulders, falling down to her knees. Emily stepped out of the dress, kicking off her heels in the process. She was wearing white, lacy lingerie. Her skin glowed with health.
"Wait a minute," said Emily. "This is totally unfair. I'm almost naked and you're not. I think I should fix that." She walked around me, pressing up against my back. Her arms wrapped around me and started expertly undoing the buttons of my shirt. I had long since removed my tie. Once my shirt was off, she started on my pants. My cock was as hard as it's ever been. As soon as the waistband of my pants pulled below erection, it sprang up, constrained only by my boxers. Emily came back around in front of me. She eyed my groin.
"Well, I guess we need to take care of this, now don't we. God, you're hard!" She knelt in front of me, slowly pulling down my boxers. When I was completely free from my fabric fetters, Emily studied my member. I was endowed with about 5 and a half inches, nothing extraordinary.
"Not an ugly dick, by any means. Nice length, color..." She ran a finger along the underside of my shaft, and it twitched. Emily giggled, her cheeks turning red. "You're certainly happy to see me, huh?" She licked her palm and reached for me, gripping my rod in her warm hands. She began gently running her closed hand up and down, twisting ever so slightly. It felt heavenly. I looked down at the lingerie-clad goddess in front of me. She was completely engrossed by her task. Her amber eyes were focused on one thing: the hard-as-a-rock member in front of her. Eventually, Emily stopped her action. I looked at her, puzzled. She was holding my rod near-vertically, moving her head towards my... oh. Emily ran her tongue up my dick, making me shiver with pleasure. She licked up my shaft, sometimes fast, sometimes slow. Again, she stopped. I leaned my head back; I couldn't wait for what would happen next. Emily let go of my cock. I felt something warm and soft slide over my glans. I looked down at Emily, seeing her lips wrapped around my member. She began moving back and forth, not missing an inch between the ministrations of her tongue and lips. Her hands explored my groin, running through my pubic hair and fondling my ballsack. As Emily pushed my rod deeper and deeper into her mouth, I felt a warm feeling start creeping from my balls to the tip of my cock. The next three things happened near spontaneously: I moaned, my dick jumped, and I came. Emily, feeling the twitch, had pressed 3/4 of the way down my shaft and ran her tongue over my glans, guiding the sudden onrush of semen into the back of her throat. She retracted from my sopping rod and swallowed. Then she burst out laughing.
"God, I've always wanted to do that!" I couldn’t help but smile. She was just so adorable. I pretended to play dumb.
"What, exercise total control over a man?" She kept on laughing, pausing only to choke out: "No, doofus, suck you off! I've fantasized about you so much..." That made me pause. She, the hot one out of the two of us, fantasized about me?
"Well, now it's MY turn to make YOU cum!" I grabbed her and lightly tossed her onto the bed, with her legs hanging over the side. She giggled.
"I won't feel bad if you can't get me off," she said. "After all, technically, we're still virgins." I took that as a challenge. I slid her soaked panties down and knelt between her legs. She had a landing strip of dark pubic hair that led to beautiful labia. Her pussy was perfect. I started with one finger, slowly pushing in. I didn't feel her hymen, and it didn't surprise me. She'd just confessed to pleasuring herself regularly. I added another finger. As I probed her warm sex, I noticed one spot that seemed to make her jitter a bit. I prodded it lightly, and sure enough, it elicited a moan.
"Y'like that, Em?" She didn't bother replying. I took that as a yes, and pulled my fingers out of her snatch.
"Why did you stop, Andrew? That felt amazing!" I chuckled to myself, before putting my lips to her pussy. I snaked my tongue in between her puffed-up labia, heading directly for the spot that she loved. With one hand, I reached up and began playing with her clit. Her fluids were warm and sweet. My tongue continued to poke at her G-spot, inciting a few moans from the owner. After a few sweet minutes of tonguing and tweaking, she came. Her pussy contracted around my tongue, leaking warm liquids onto my face. I stood up, took her hand, and helped her to her feet. She seemed a little unsteady for a moment, but regained her composure quickly.
I leaned in and our lips met once more. I reached around her and fumbled with her bra strap. Eventually managing to undo the (simple) clasp, I pulled her bra off, exposing her breasts to the air. About the size of a ripe orange, each of her tits was adorned with a light brown areola, topped with a small, pert nipple. We pulled away from each other, the taste of her lips still lingering on mine. I looked at her, fully nude for the first time, and couldn't help but feel privileged.
"Damn, Emily. You're gorgeous!" She blushed and looked down at her feet. A trickle of vaginal fluid leaked down her leg. Her hair shone, her eyes sparkled, and her smile lit up the room. I was sure lucky.
"Emily, I think it's time we... did what we came here to do." She giggled.
"You can say the phrase, "have sex", Andrew. It's not gonna kill the mood, I promise." I picked up the little vixen in my arms and sat her on the bed.
"I want to be on top, Andrew. You owe me at least that much." I shrugged. As long as we fucked, I really didn't care. I lay back on the bed. Emily straddled me, rubbing her labia against my member. She slowly grinded back and forth, wetting my cock with her juices. Once I was sufficiently wet, she rolled a condom onto my shaft. Then she raised up, pointed my erection right at her snatch, and slammed down. Oh, God, she's hot. Emily must have guessed what I was thinking, and grinned.
"I bet you won't last five minutes in my pussy, Andrew." I grinned back.
"You're on!"
She quickly developed a rhythm, steadily pumping up and down on my cock. I got to see her tits jiggle as she rode me. Emily leaned forward as she rode, not slowing at all. I ran my hands down her back, feeling her smooth skin underneath my fingers. Her hair brushed against my face, and her warm breath tickled my nose. Our lips met once more in a passionate dance, the rhythm of our lovemaking steadily continuing.
As it happened, I lasted seven minutes. I orgasmed right on her downbeat. I shot cum into the condom, sending it right back down at my cock. Emily pulled off of my shaft, looking at the mess I had made.
"Okay, you lasted longer than five minutes. Soon as I clean you up, you can choose the next position." I knew what I was going to choose. Emily unrolled the used condom from my cock. She sucked all the cum from my cock, allowing me time to regain my erection in the process. Once my member had been sufficiently sanitized, Emily smacked a fresh condom on me.
"What do you wanna try, Andrew? I’ll do almost anything." I grinned.
"Doggystyle." She laughed.
"I forgot, you're an ass-lover." She got on all fours on the bed, pointing her round rear in my direction. I got into position behind her, resting my rubber-wrapped member on her back.
"What are you waiting for?" She demanded. "Come on and fuck me!" I obeyed immediately, pushing my erection into her waiting pussy. God, this was even better than before. I ran my hands over every inch of skin I could reach. With each thrust, my balls slapped against Emily's crotch. I could hear her breathing getting harder and knew it would take only a few minutes to make her cum. With one free hand, I squeezed her ass. With the other, I reached around her leg to finger her clit. After about 30 seconds of my multiple ministrations, she came, collapsing her front half onto the bed and panting. I had cum twice already tonight, so I kept going.
A few minutes more in her pussy and I was about to blow my load. I pulled out. She looked back at me, puzzled. I didn't bother explaining, choosing instead to quickly remove the condom and jerk my cock. Recognition dawned in Emily's eyes, and she said, "Don't bother jacking off; hump my ass until you cum." I did so, rubbing my raging erection between her ass cheeks until I came, sending a few beads of semen flying onto her back. I flopped back onto my bed, utterly spent. The phone rang, suddenly. I picked it up.
"Andrew, it's dad. I convinced your mom to get a hotel room tonight so we can have some fun of our own. We won't be back until noon tomorrow." Emily looked at me quizzicly.
"Who was that?"
"It was my dad. He and my mom won't be back until noon tomorrow." She laid back onto the bed next to me. Soon, after a few minutes of sparse chatter, we fell asleep.
I woke up the next morning to a slurping sound. I looked down and saw Emily bent over, sucking my cock, with her ass up in the air behind her. Damn, it was a good blowjob.
"Emily, I love you."
"I love you too."

8 years later...
"Do you take this man..."