Who Will Pop My Cherry For Me?

I was a sophomore in college and still a virgin, and I wanted someone to do the nasty to me—you know, pop my cherry—but who?

My college roommate, on the other hand, lived for sex. And I never knew how she maintained her 3.6 GPA, because she never was in our room except to shower, sleep, and... fuck. Almost every night some guy fucked her. Sometimes it was the same guy, but mostly, it was someone different.

It didn't matter that I was there, trying to study. She'd pop her head in and ask if I was alone—I always was—then she'd lead the bugged-eyed guy to her bed where they'd make out for a while, undress, and fuck.

Nancy had looks to die for: long, wavy blonde hair, beautiful face, blue eyes, big boobs, tight ass, and nice hips. Boys trailed after her like bees to nectar. So after a while, the constant troop of one-night-stands numbed my sensitivities.

At first, I tried ignoring the activities across our room, but soon, I curiously watched how they fucked. Each guy had a different technique: some kissed first; some ate her pussy first; some went straight to fucking and went in her from the top, side, or doggy; some wanted her on top, pogo bouncing; some were playful and some were rough; some lasted longer than others did; but most didn't take Nancy to her climax, leaving her too soon, wanting more, panting for more. I'll hand it to her, though, she always insisted on a condom and turned away any guy who wouldn't agree or tried the anal approach.

During one of her periods—she never fucked during her periods—I got the courage to ask her about her sex-life.

"Nancy, would you mind if I ask you a personal question?"

"You'd like to know why I fuck so much, right."

Her straightforwardness took me by surprise. "H-How did you know that's what I was going to ask?"

"Was written all over your face, Dory. You'd never make a good poker player."

"Okay, then... Why so often, any with so many different guys?"

"For one thing, it feels soooo good... No, it feels soooo damn good, better than anything than I could ever put into words. And second, I'm searching for Mister Right, the perfect sex-partner. A six on a scale of five—I haven't found him yet."

"So, you keep looking?"

"Yep. And I'll fuck every guy on campus if I have to."

"But isn't there more to life than fucking?"

"Not while you're young. When you're older, you can slow down, but for now, I'm gonna keep fucking."

"I noticed a wide variety."

"Yeah. At first, you tried to ignore us, but after a week or so, I caught you sneaking a peek, and after a while, you sat and watched until the guy finished. Then you'd go back to your books and act like nothing had happened. But I saw you."

"Yeah. You caught me."

"You ever been fucked?"

I cleared my throat and squirmed in my chair.

"You're a virgin, aren't you?"

I blushed. "Y-Yes. Please don't laugh."

"Dor, we all were, once. Nothing to be ashamed about."

"Thanks."

"How long you wanna stay a virgin?"

"What you mean?"

"Just what it sounds like. I know a lot of guys, good guys, who would be very gentle when they popped your cherry."

"I don't know."

"Let's do this: While he's humping me, I'll rate each guy from zero, my closed fist, to a high-five. You record the five's names. When we find a suitable team—say ten—I'll give each of them another go around and rate them again, much stricter that time. The top-rated guy gets to pop your cherry; I'll be there holding hour hand so you won't be alone. Once the deed it done, he can ride you to your climax, while the second top-score and I will do the nasty in my bed. Then it's the SS--Sex-Sisters forever. What do say to that plan?"

I took a deep breath. "O-Okay. When do we start?"

"As soon as my period ends."

* * * * *

"Okay, SS. Tonight's the first night. Got your spreadsheet set up? My pussy's ready."

I started up my computer, loaded a blank Excel spreadsheet, and labeled the columns. "I'm ready. Gee, I'm tingling just thinking about it."

"Wait till you feel a big cock between your legs; there's nothing like the waves of passion that crash upon you from head to toe. You're going to enjoy this."

"I hope so. I'm scared, as well."

It wasn't long before Nancy returned with the first guy in our quest to fill the roster for our Team of Fives. "Larry, this is my roommate, Dory. Don't mind her while we fuck; she's always got her nose stuck in a book and doesn't notice anything but formulas and thingies like that." Nan winked at me.

"Hi, Dory. Glad to meet you. Sure we won't disturb you."

I'd dressed as frumpy as I could, left my hair a mess, and scrounged a pair of dark-rim glasses. I looked up from my book, pushed the glasses off my nose, and said, "Larry, is it? Have fun, you two." And looked back to my book and bit my lip so I would burst out giggling. My insides were a flutter with excitement.

Nan took Larry by the hand and led him to her bed. I watched them undress, Larry's cock respond to Nan's stroking, and her writhing as Larry did his best to score high—although, he had no idea what Nan and I we up to. Poor sap. Larry had just gotten started when Nan held up her hand: three fingers. In the excitement, I'd forgotten to start my computer, but three fingers wouldn't make the team, anyway.

So it went, night after night, Nancy introduced me to the guy who was going to fuck her, I'd record his name, and after he shot his wad, Nancy signaled his score. If it wasn't a five, I deleted him. By the time Nancy took a break for her period, we'd only collected four names that she'd rated as a five.

"I don't know what to do, Dor. The guys aren't up to my high standards and yours, and I'm not willing to dilute to pool for the sake of numbers. What you think? You're the one losing her cherry."

Until now, this had been like an academic exercise, a psychology experiment in human sexual behavior, but all of a sudden, it became quite personal. We were ‘shopping' for the best fucker Nancy could find, and I was the fuckee. "I-I think we should go for quality over quantity." My insides were churning.

"I agree. My first time was with a clumsy pecker-head in the backseat of his car, came as soon as he popped my cherry. What a mess he made, all I got was pain, his cum all over me, and a horrible memory. I don't want that for you, Dor. I want you to look back on your moment with warm, fond memories. It's the least your SS can do for you."

"Thanks, Nan." I touched her hand, and she squeezed mine. I looked into her brown eyes and saw my reflection. She slid closer to me and cocked her head. Her lips were swelling; she licked them. I licked mine. I tasted her hot breath when our lips met and our tongues explored each other's mouth. We embraced. I kissed her neck and ears; she kissed mine.

"Damn my period," Nancy said as she broke away.

"That was nice, but I still want a cock to pop my cherry."

"And I'll find you the best one on campus, SS."

Spring Break was rapidly approaching, and we had only six names on our Team of Fives.

"Only six guys measured up? I thought there'd be more. I sure enjoyed myself more than six times."

"But you only rated six of them with a perfect score."

"Then stage two will be easier: If I spread them apart, I could re-rate three on Saturday and three on Sunday."

"Can you handle three a day?"

"Sure. They do all the work; I'll insist on the modified missionary position, that's how you should do it your first time."

"Okay, Super Pussy Weekend," I blurted and blushed.

* * * * *

By Sunday evening, Nancy looked pooped. "Tired?"

Nancy sat on the edge of her bed, chin in her hands. "Yeah. Six guys is harder work than I figured. How does a hooker do it? How many fives this go round?"

"Two."

She looked up, eyes widened. "Two?"

"Yep. Two."

Nancy flopped on her bed. "I can't do this again. You pick which one you want, and I'll take the other."

I checked my notes. "I liked the way John was so gentle with you. I'll take him. You can have Bill."

She put her arm across her forehead. "Done! I'll set it up with the guys for next Saturday. They'll know what's what so don't be scared or embarrassed."

Yeah, right. Don't be scared or embarrassed. Impossible. Why did I agree to this?

* * * * *

My pulse was racing as I stood toweling myself after a shower. I blew-dried my hair and put on some makeup, but not too much. Nan said to wear something sexy. What did I own that was sexy? A yellow, cropped, tank tee—no bra, my c-cup boobs don't need one—and a pleated, yellow, mini-skirt with lacy, black bikini panties. I checked in the mirror: my nipples were plainly visible and my tight ass was, as well. That's as sexy as it gets.

I paced but didn't have to wait long. Nancy stuck her head in the door and said, "Indecent, I hope." The guys behind her chuckled. I gulped.

Nancy entered with the guys trailing. "Dory, this is John. He won the cherry prize for this evening: you. And this is Bill. He won the consolation prize: me."

"Hi, Dory," they said in unison.

I blushed. "Hi, John. Hi, Bill."

"Didn't I meet you before? You look so different tonight," said John.

"A girl's gotta try." Why did I say that? It was so lame.

We gathered in a circle. "Well, guys. Here are the rules for tonight. Bill and I are here to add emotional support for my dear Sex Sister on the occasion of the ‘popping of her cherry.' John will do the honors. However, in case John falters..."

"Hear... Hear..." said Bill.

"Bill, his second, will rise to the occasion and complete the deed. Is everyone understood?"

We all nodded.

"Fair maiden, Dory, are you ready?"

I stood ridged. "Y-Yes."

"Sir John, remove her garments."

John stepped forward and looked in my eyes and kissed me. He reached under my top and caressed my boobs and kissed me, again. I kissed him. Finding my nipples, he gave them a tweak. They recoiled and then hardened. His tongue pushed passed my lips and toyed with my tongue. My breathing deepened. My pussy twanged. Then he lifted my top over my head and showered my boobs and nipples with kisses. The sound of his suckling was maddening, and my crotch was alive.

His hand slid down to the button on my skirt. It fell to the floor. As if they had eyes of their own, his hands found and untied the strings to my bikini panties; it slipped between my legs to the floor, as well. All the while, he suckled my nipples like a hungry new borne baby. My pussy was crawling with passion.

I stood naked before them, and all eyes were on me, but I didn't care.

"Well done, Sir John, thou mayest disrobe too, as shall we. Sir Bill, disrobe me.

As I watched, John pulled his tee over his head and dropped it on the floor. I gasped. His pecs were massive, his shoulders were broad, and his abdomen rippled. OMG! He was handsome.

Then he unbuttoned his cargos, unzipped the fly, and pulled them down, across his enlarging cock. When they fell to his ankles, he stepped out and kicked then aside. I fixated on the bulge in his boxers. That was going to be in my pussy before the night was over, and I wanted to see what I was in for—no pun intended.

When I saw the size of the growing bulge, it took my breath away. Absentmindedly, I began massaging my boobs and fingering my pussy. He was watching me, as well, rubbing the bulge in his boxers. Then in one swift action, he pulled them down, stepped out, and tossed them aside.

His cock was free to move where it may, and with each beat of his heart, it was bending and bobbing upward, getting harder and bigger. Is it going to fit? I thought. I trembled with anticipation and fear. It had fit in Nancy more than once, so it should fit in me. It's just nerves, I told myself. Gazillions of women have lost or will lose their virginity. It's no big deal.

Nan and Bill, who was also stiff as a board, stood on either side of John.

"Sir John, are you ready to slay the dragon and rescue fair maiden, Dory, from her virginity?"

John looked to Nancy, bewildered. "Slay the dragon?"

Nancy pointed to my crotch. "Pop her cherry. Get with, my boy."

John grasped his throbbing cock in this hand. "Yes, I am ready."

"Is your trusty sword at the ready?"

He stroked himself several times, and then said, "It is, ma'am. It surly is."

"Then help me, Sir Bill, as we usher maiden Dory to yonder bed."

They took an arm each and walked me backwards to the middle of my bed.

"Sir Bill, follow my lead. With one hand behind her shoulder, gently lower the maiden to the bed, with the other under her knee, lift it high to present her virgin pussy to Dragon Slayer. Now spread her wide; stretch that pussy. Sir John, approach with thy mighty sword to heaven's gate and..."

Nancy abruptly dropped my leg, dashed to her bedside table, and returned with supplies in hand. "I forgot lube and condoms. Here, John, put one on, lube yourself, and her pussy; lube her good. Okay, where was I?" She lifted my leg in position.

"All kidding aside, John. If you hurt her on purpose, you'll provide the balls for the next spaghetti and meatballs dinner. You got that?"

John, without taking his eyes off my pussy, nodded. "I got it, Nan. I'll be gentle."

"Okay, Dor. He's gonna put his cock in until he hits your barrier. That's your cherry. Go ahead, John. Squeeze my hand, Dor."

"Mine, too," said Bill.

Nancy and Bill leaned over to watch until their heads bumped.

"Hey, guys. I can't see with your heads in the way. I don't want to peter out before I get the deed done... Okay, I'm there."

"Okay, SS. This will hurt a bit, but John will make it quick When he's popped your cherry, we'll access the damage. Go for it, John."

John leaned into me, and his cock ‘popped' through my barrier. I thought I heard the pop, but it was more of a feeling than a sound. The pain didn't last very long, but then, John stopped as instructed.

"How you doing, SS? How's your puss feel?"

"Pain shot through but it's okay now."

"Try some gentle hip action, John."

John rocked hips, moving his cock in and out of me.

"How's that feel, Dory?"

"Tender, but okay."

"I think she's good to go. Swing her around on the bed, and take her to pleasure heights like those that she'll remember forever. Make her cum as often as you can, John, and I'll promise you a special week."

As John helped me reposition in bed, he looked at Nancy. "What if I like fucking Dory better than you?"

Nancy shrugged her shoulders. "Then she's my prize to you: a win-win all around. Come on Bill, all of this fucking has made me horny."

Bill's cock was engourged, and he was stroking it. "Me, too."

John was quite gentle with me; he didn't rush. He knew every spot on my body where nerves were connected to my pussy. So every kiss on that spot on my neck was almost as if he was kissing my puss. As he move from spot to spot, my pussy became more excited. Masterful is a word that's been overused, but that described John.

His gentle rocking encouraged me to match him, and together we climbed the passion mountain. He knew when I was ready for my first-ever climax—I didn't know—and he took me there, and the emotions and electricity of the moment exploded in my brain. I never wanted to descent that mountain of passion, yet eventually I did, but John took me to another mountain top greater than the last one, and we came together. Jolts of passion shot from clit through my spinal cord to my brain, exciting every muscle and organ system along its way. His hips jerked with each load of hot, sticky cum spurting from the pulsing head of his enormous cock. Not once, but several times—I lost count.

Then he collapsed on me for a moment or two, and said, "Cross your legs, I've got more to give."

I did. Although his cock was shrinking, he was erect enough to excite my clit to yet another most marvelous climax and several more mini-climaxes. OMG! John's a sex god! I want him for myself, I thought. I didn't know the first thing about blowjobs, but as soon as John extracted his cock, I whipped off the condom, went down on him, and started licking and sucking like a new-borne calf on a teat.

John laid back and half grimaced and half smiled. He motioned for me to swing around so he could toy with my pussy. It wasn't long before, John's cock awakened enough for another fuck. By now, Nancy and Bill had their climaxes and were standing by my bed, watching us. As John lowered onto and into me—we didn't stop for a condom—I glanced at Bill feeling Nan's pussy, and Nan stroking Bill's new boner. Out of the corner of my eye, Nancy was leading Bill back to her bed, his cock in her hand.

This time around, John took it slower, showed me new positions, and found new ways to climax me, again and again. When we were finished for the evening, the guys lined up to say their goodbyes, Nan asked, "Well, John. Do I owe you a week of special privileges or not?"

John looked at me and winked. "Not to sell you short, Nan, but Dory's a better fuck than you."

"I figured it might be that way. Well, Bill, I guess it's you and me kid."

"No hard feelings—no pun intended."

"None, except the one in my pants," said Bill.

Nancy leaned over, kissed Bill, and reached into his shorts. "Bill, you animal. You want me to take care of that before you go?"

Bill nodded. "Only if you want to."

"I'm an animal lover from way back. If you two would excuse us, I've got some loving to do."

John and I looked at each other and smiled. He leaned toward my lips, and we kissed. OMG! My pussy fluttered. I embraced him and kissed him back. He hugged and pressed against me. His cock is enlarging. I lifted my leg and rubbed it. It's getting bigger. He squeezed my boob and nipples. I tossed my top aside; he tossed his top aside, as well. I pressed my boobs into his chest. The bulge in his cargos is rubbing my crotch.

I dropped my skirt; he dropped his cargos and boxers. He untied my thong string; I pulled his cock and tucked it between my legs. John reached and picked me up, my knees bent, calves resting on his arms. I held on to his neck as he impaled me on his rock-hard cock. No time for a condom this time either. WTF, anyway? Once completely inserted, John lifted me up and down on his cock. As I matched his rhythm, I rocked my hips, and he rocked his. The feeling was indescribable, and again, a new climax experience awaited me. John was magnificent.

He put me down, I cleaned up cum, and we dressed, we kissed and said our goodbyes. John kissed me on my nose as he left. I lingered at the door and watched until he turned the corner. After closing the door, I leaned against it and sighed. It was then; I noticed Nan and Bill had been watching us all along.

"You two put on quite a show," said Nan.

"Yeah, you sure did. I almost got hard, again," said Bill.

"Down, boy... You and John seem to have hit it off... Time to get dressed, Bill."

"Yeah. As you said, it will be a night to remember, forever. Thanks, SS."

"What's this, SS stuff," asked Bill.

"It's time to leave, Bill. See you tomorrow night."

"Sure, tomorrow."

Nan gave Bill a quick peck on the lips and closed the door.

"Bill fucks like a mink and is about as bright as one. Now, what about John?"

"He was great. Mister Wonderful. How can I ever thank you?"

"How about a kiss?" Nan smiled, cocked her head, and wet her lips.

When our lips met and our tongues intertwined, my pussy came alive again. My nipples were erect, as were hers. I kneaded her boobs and tweaked her hard nips. She slid her hand to my clit and rubbed. Her touch filled my body with electricity; she knew where to touch and exactly how to do it as only a woman would know. I touched her wet pussy and explored her private parts, as well.

We both loved men, wanted men, desired men, fucked men but each appreciated a woman's touch, occasionally. After a most wonderful climax, Nan said, "Maybe you can help me find my perfect six out of five."

"I'll give it the old college try."

We both laughed and kissed good night.