I Dare You

Chapter I

Jenny looked down between her splayed legs and I felt a slight frisson travel up her small frame. I had mounted her and my huge cock, brick-hard and straining inside a Trojan Magnum XL, was aimed at her pussy. It was a sunny Thursday afternoon in September, and we were lying naked on top of the tattered Air Force blanket on my bed. Dad was away on business, Mom was at the nail salon, my twin brother Danny was at the gym, and our housekeeper, Inez, was running errands. For an hour or so, Jenny and I would have the house to ourselves—plenty of time for a good, long fuck.

I had been wanting to drill Jenny for a long time—at least a week. (The attention span of a teenage boy is very short, even when it comes to sex.) She was the only varsity cheerleader I hadn’t boned. Petite and nicely tanned, she had a cute, almost doll-cute, face framed by ash-blond curls, and she also had a set of nice C-cup tits. They were full and round like the rack on a Playboy centerfold. They were not as big as I preferred, not big enough for tit-fucking, but they were okay.

Gazing at my 11-inch prick, which she had just given a mediocre blowjob and then slathered with lube, Jenny gripped my arms.

There always comes a certain moment—like this one—right before I slide my cock into a girl for the first time. She lies on her back, spreads her legs and I get on top of her. Then she looks down and suddenly realizes the size of the meat I’m about to stuff into her box. Her breathing stops and her blood runs cold. She is afraid—truly, physically afraid.

Each woman reacts a little differently. Corinne, a gymnast, scissored her legs flat on the bed, as if that would open her pussy a little more. Becky, whose parents were hippies, did some kind of meditation. Anna, a busty paralegal I met at my father’s company holiday party, threatened to sue me if I “damaged” her. Summer, who attended a Catholic school, made the sign of the cross.

Of course, they all tell me to go slow at first, and they all say something like, “It might not fit.” This is only natural. No woman would say, “Don’t worry, I’ve fucked a lot of guys so my pussy’s nice and loose. Drive it home!” As humans, we hold on to our dignity as long as we can.

“Oh, Billy, go slow at first,” Jenny said, staring at her beaver. (Told you.) “I’ve never had one that big in me.”

“Just relax, honey,” I said. I kissed her on the forehead and she curled her arms around my chest. I reached down, grasped my tool, and guided the head into her. She was tight, but not that tight. Rumor had it she’d done her share of fucking. Her face scrunched in pain and she seethed through her teeth. “Oh, my god, Billy. Oh, god, it hurts.”

“It’ll feel okay in a minute. You’ll be glad we kept going.” I gave her a couple more inches and she tensed her grip on my back.

“Easy, Billy, easy.”

While she nuzzled me helplessly, I glanced down. About five inches of my cock was inside her pussy, with the other half-foot, up the air. I was glad to have such a monster dong, of course, but just for once I wanted to feel the whole thing go home, to feel my big nuts bouncing against a girl’s ass while I fucked her.

Not this time. At inch number seven, or thereabouts, I hit her wall. “OHHHH!” she exploded in my ear.

I started giving her slow, short strokes and her initial cry gave way to gasps and whimpers. Her boobs jiggled and I craned down to give the left one a horny lick. Then I picked up the pace. The mattress began to bounce.

“Good, isn’t it, baby?” I asked her.

“Oh, yeah,” she said between moans and labored gasps.

Of course it was good for her. I was doing all the work. She didn’t lift her pelvis to meet my thrusts. She didn’t reach down and squeeze my balls or talk dirty. She didn’t even raise her head to look down at the action. She was just lying there and enjoying a nice, perfunctory screw. She had recently celebrated her 18th birthday and was getting lazy in her old age.

After a few minutes, I suggested she get on top but she was afraid. Considering our mismatched sex organs, she was probably right. She did let me fuck her doggy-style. She came, lamely, almost as soon as I put it in. Now she was even more passive, and I was getting bored. I wanted to shoot my load and go have some grapefruit juice. I looked down at her young back, smooth and straight, her mid-sized breasts bouncing back and forth.

Then, for a split second, I saw another body in her place—a bombshell, a goddess of Jayne Mansfield proportions and beyond. A voluptuous, womanly figure, tall and long-legged. Massive, firm tits heaving. A trim waist. A full, succulent ass slamming backward to meet my thrusts. A shiny, Nordic-blond mane tossing and whipping, and a Scandinavian accent intoning “Oh, ya, Billy, fock me, honey. Fock me gud!”

That was all it took. A bolt of lightening ran up the base of my dick. I groaned and felt the first shot of semen squirt into the condom. Then, another, bigger one. Then another and another. I blew big wads, but this one was truly prolific. I began to worry the condom would break, even though I’d left plenty of room at the tip.

I pulled my cock out of Jenny and stroked it, watching the end of the condom swell with milky gel. It looked like some kind of translucent blob attached to my glans. Still jacking my thick shaft, I felt one last heavy surge.

Then, with a wet pop, the condom split open and my jism splattered all over Jenny’s back. She was covered. Some was in her hair, and a dribble ran down over her hip.

“Ewwww!” Jenny squealed, arching her back in disgust. “You came on me!” She glared at me over her shoulder and craned to see the juice on her.

“The condom broke,” I said. “You’re lucky I pulled my cock out of your pussy in time.”

“Gross! It’s all over me! Oh, fuck it’s in my hair!” While she continued to bitch, I ran to the bathroom to dump the condom and get her a towel.

Y’know, it’s not like I’d spilled battery acid on her. One of the many things I’ve learned about women, however, is that if a girl doesn’t like cum, she’ll never like cum. Something like that isn’t open to negotiation.

Well, at least now I’d fucked every cheerleader, I thought as I wiped the spooge off her. I cleaned her up quickly and calmed her down with an impromptu back massage. I give good massages. She cooed appreciatively and talked about us doing a chemistry project together. Hadn’t we just done that?

Then I remembered the vision that had brought me to orgasm. That incredible body, that sexy Swedish voice. I felt a queasy rush of guilt in my gut. It wasn’t the first time I’d had that fantasy.

I shouldn’t be thinking about my mother that way—no matter how hot she was.

 

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