squareroot

1.
I'd been living in New York just over a year; I'd finally found somewhere I really knew I belonged. When I first stepped off the bus deep into the bowels of the Port Authority Bus Terminal, I was a lost girl; broke, alienated and socially retarded. Now I had my own little studio apartment in Brooklyn; a decent job rewriting code for old ATM machines, and a few good friends. No sex life, no dates; not even the prospect of one. But in general, life was alright.

My friend Jim emailed me to let me know that he was thinking about moving out here, and wanted to know if he could possibly stay in my apartment for a while.

Of course he could. I remembered how stifling our little Midwestern town could be. I remembered what it was like to live with your mom and dad. Jim could stay with me as long as he wanted.

So Jimmy showed up on my stoop one chilly and frosty Saturday morning in January, looking tall and cold and a little lost, all his stuff packed up in a gym bag at his side.

Jimmy had originally been more my little sister's friend than my own. He was in his early twenties, seven or eight years younger than me, and he was taking a break from college for a while to figure out what he really wanted to do with his life. I had had idle fantasies about jumping his bones for years, ever since Alexandra first introduced us, and of course the idea of having him under my very own roof totally brought out the pervert in me. But I pretty much dismissed that thought right away. Jim has a beautiful body, long and lean; and I am not a pretty girl.

I set Jim up on the futon in my living room. Quarters were tight, but he seemed happy, and it was really kind of nice to have him around. I couldn't wander around the place topless anymore, and I had to get dressed right away after showering; but I could always lock myself in my bedroom and jill off to internet porn, so it was ok.

Jimmy got a job waiting tables, and made some friends of his own, so after the first couple weeks I didn't see him nearly as much. And I was pulling a lot of long days at work myself.

So it was kind of a surprise (to both of us!) when I came home early on Friday and walked in on Jimmy, sitting in front of the computer in my bedroom with his pants around his ankles and a hand wrapped around his (quite sizeable!) cock.

"What are you doing?" I blurted out without even thinking.

"Um, what does it look like I'm doing?" His face had turned a bright red. I felt kind of bad for embarrassing him like this.

"Well don't stop on my account!" I told him.

"Are you serious?" his hand started moving again between his legs. Between each stroke I could see the purple head of his cock. There was a fat little droplet of clear precome balanced on the end, leaking out of his pee-hole. It quivered as he moved.

"Sure," I said, trying to sound totally nonchalant, "Why not? Everybody does it, right?"

On the monitor, I could see that he was looking at one of my favorite porn sites. Punk rock girls with piercings and tattoos frolicked naked on the screen. Jim's hand had never really stopped moving, and he wasn't blushing quite as deep a shade of red anymore.

I turned as if to leave the room. "Just don't get any come on the keyboard, ok?" When girls masturbate in front of the computer, they just leave damp spots on the chair.

"Don't worry," he said, "I'll be careful."

I stopped in the doorway with my back to him. "You know," I said, "I've got some lube if you want it."

"Really?" he asked, "That'd be great."

I'd never actually watched a guy masturbate before and honestly, even though I knew it was weird and perverted of me, I was a little bit fascinated. Ok, more than a little bit fascinated. I thought it was pretty fucking hot. I didn't really have that much firsthand experience with the male anatomy; I'd slept with a couple guys in college, but it had always been dark and socially awkward and there had been alcohol involved. Back in Ohio, I'd been all about the girls, until indiscretion got me fired and more or less run out of town. Ever since I'd been in New York my sex life had consisted of double-A batteries for my vibrator and a high-speed internet connection. Not that I'm complaining or anything.

Trying not to stare, I walked over to my bedside table and pulled out the little bottle of AstroGlide that I keep in there. On my computer screen, a blonde girl with Chinese dragons tattooed up and down her arms was wearing nothing but an unzipped leather jacket. Her nipples were pierced and her pussy was bare.

I tossed Jimmy the bottle, and watched as he coated his dick in the clear syrupy liquid. His erect cock looked even nicer all wet and slippery.

"Do you mind if I take off my shirt?" he asked.

"Ok," I replied, standing stupidly in the center of the room watching as he pulled his t-shirt off over his head.

Jimmy was a hotty, no fooling. He was tall and lanky and had a nice smooth chest with pointy little brown nipples surrounded by circlets of hair; and a black triangle of hair at his crotch with a faint little treasure-trail leading up toward his navel.

I took a deep breath. "Do you mind if I just watch?"

"Um," he said blushing again, "I guess I don't mind if you don't mind." He was really cute when he blushed like that.

I took a couple cautious steps closer to him. I could tell that I was soaking wet inside my panties.

His hand was moving faster and faster, squeezing his cock tight. I noticed that he wasn't even looking at the girl on the computer screen; his eyes were fixed on me. His stare made me feel deeply self-conscious. But I couldn't leave the room, I couldn't take my eyes off of him. This was way better than any internet porn.

I felt unbearably awkward and shy. I felt my cheeks burn as the blood rushed to my face. I was the one who was blushing now.

"Would you mind taking your shirt off too?" he whispered, "If you don't mind. That would, you know, help."

I nodded, biting my lower lip hard, threatening to draw blood. Slowly, hands trembling, I unbuttoned my blouse. I unsnapped my bra and without ceremony let it fall to the floor. My breasts were flushed with excitement, and my nipples were all hard and pokey-outy.

I personally don't think my boobs are all that. They're not small, but their not that huge either, and the nipples tend to point off in opposite directions. They are sensitive though; often when I masturbate I like to suck on one nipple while I bring myself off.

Apparently that was enough for Jimmy. His hand was like a fucking piston on his cock. His delicate balls were drawn up tight and jiggled deliciously with every stroke. All of a sudden, his whole body went rigid. His stomach muscles clenched sexily and he groaned out loud, a long, soft, guttural growl. Semen spurted out the end of his engorged dick, all the way up past his navel and onto his smooth chest. Gob after pearly gob pumped out. That was a lot of come!

His hand slowly stopped pumping as his cock wilted in his fist. He gently milked the last drops of come out of the end of his tool. There was a huge puddle of come on him, stretching from his pubes, filling his bellybutton, spattered drops flung all the way up to his chest just below the nipples. I was so horny I thought I might come just squeezing my thighs together.

We stood looking at each other for a long moment, just breathing. I hadn't realized how close I had gotten to him while he had been doing it; I could feel the heat radiating off his very nearly naked body.

Without saying a word, I extended one index finger and dipped it in the big pool of ejaculate on his belly. It was warm and sticky. I brought the finger to my mouth and tentatively licked it off. It was bitter and salty, and reminded me of rice pudding. While it wasn't exactly delicious, it was almost unbearably sexy. I'd never tasted boy come before; I decided that I didn't mind it at all. Not even one little bit.

"You should go take a shower," I said. Jimmy wordlessly stood up, his fat cock hanging heavily between his legs. "Don't put your pants back on, you'll just get come on them. Go, shower!"

He stepped out of his crumpled pant legs and walked out of the room, slowly, almost as if he was in a trance. Fuck me, he had a cute little ass on him too. As soon as he shut the bedroom door after himself, I pulled my own jeans down. I didn't even bother grabbing my vibrator. I just knelt by the side of the bed, jeans and panties around my calves, and rubbed my swollen little clit like a maniac. I came hard and fast: two, three times in a row, moaning into my bed sheets. It was intense.

2.
I didn't actually see Jimmy again for another two days; I had to be at work before he even woke up, and by the time he got home I was usually already in bed. I played the incident out, over and over in my head. It made excellent masturbation fodder. Since he'd come to stay, I hadn't been using my vibrator; I'd always been afraid that he'd hear the obnoxiously loud buzzing of it's little motor through the paper-thin walls, and know exactly what I was doing. I stopped worrying about that. Actually, I half-hoped that he did hear me.

When I got home Friday afternoon, he was curled up on the futon reading a book.

"Hey Dude," I called as I walked in the door.

He blushed (how cute!) and put down his book. "Hey."

I came in and sat down on the end of the futon. "Listen," I said, "about the other day Was that too weird for you?"

"I meant to apologize to you for that." he said sheepishly.

"You don't have to apologize for anything!" I said, "You can look at porn on my computer whenever you want. Just don't get any viruses on my machine."

"Ok" he said.

"Or get come on the keyboard."

He laughed.

"So listen" I said.

"Yeah?"

"Do you feel like doing it again?"

"Now?"

"Uh, yeah. If you feel like it."

He was already unbuttoning his jeans. I noted with satisfaction that there was a nice looking bulge going on in the front of his boxer shorts.

"Would you take your top off again?" he asked as he kicked his underwear off.

"Sure," I pulled my sweater off over my head and wriggled out of my bra, "You should take your shirt off too."

He was naked and really hard and he looked delicious. This was really freaky. Freaky, but hot! His long, skinny body was draped on the couch right next to me, nice fat cock bobbing around for my viewing pleasure.

"You can come on my tits this time," I said shyly, "If you want to."

He knelt next to me while I lay down on the futon. I had a prime view of the action going on between his legs.

"Would you take off your pants too?"

I hesitated for a second, then shrugged. "Sure." I unsnapped my slacks and wriggled them off. I sort of wished that I had put on sexier underwear that morning; I was wearing plain white panties.

He started stroking in earnest. I loved the strong, confident way that he handled his cock. God it was sexy! It was all I could do not to shove my own hand down my panties and masturbate along with him.

There wasn't as much come as there had been the other day, but he squirted it all over my breasts, which I thought was hot as fucking hell. I spread his semen around on my boobs, stiffening my nipples, and idly licked my fingers clean. A girl could get used to that.

Jimmy was lounging naked next to me, watching. "Would you do that for me too?"

"What?"

"You know, masturbate. Let me watch."

"No!" I sucked air through my front teeth, "I'm too shy!"

He let it go at that. If he'd been just a little more assertive, I thought later on as my vibrator plunged in and out of my slippery pussy, I might just have put on a show for him. I might just have at that.




3.
It was Sunday morning, and I skipped yoga. Jimmy was still asleep, his tousled dark hair half obscured by his blanket, when I stepped into the shower. When I came out, warm and pink and moist and wrapped up in a big purple towel, he was sitting up in bed.

"Hey,"

"Hey,"

Long, stifled, uncomfortable pause. Me: "So, you feel like?"

Him: "Yeah. Yeah I do."

He pushed the blanket back. He was wearing Frosty the Snowman boxers, and his cock was making a delightful-looking snowman right in the middle of them. I let the purple towel fall onto the living room floor, felt hot and self-conscious as his eyes traveled over my naked body.

He peeled off his wintery boxer shorts, letting his big fat cock spring free. I knelt on the floor next to the bed, head cradled in my arms, watching him handle himself.

Oh God, his cock looked delicious! It was so sexy, watching him stroke himself in his strong confident hand. He was pinching one of his little brown nipples with one hand while he worked his cock with the other. I let one hand slip between my own thighs. I was hot down there, wet and slippery.

"Would you like to come in my mouth?" I asked him softly.

"You don't mind?"

Up until the other day, every encounter I'd had with boy come had ended up on the inside of a condom. But now that I'd had a taste I was an addict. It's not that it was delicious or anything if anything it kind of reminded me of snot; it's just that it was so fucking sexy!

I crept closer and opened my mouth up wide. Resting my chin on his bed sheet, I stuck out my tongue. I knelt between his legs, his thighs to either side of my ears. He laid the purple head of his cock down on my tongue. It was so hot, so alive, I nearly jumped when his flesh contacted mine. His hand was moving rhythmically up and down the shaft, gripping it with just the thumb and forefinger. His cock twitched with every stroke. Being super careful with my teeth, I gently closed my lips around the head of his dick.

He was making these delicious animal noises and I could feel his penis swelling and straining in my mouth. I wanted to swallow him whole. I wanted to jump up and grind my pussy into his crotch. I wanted to jam my cunt onto that dick.

But before I could do any of these things, Jimmy stiffened and shouted out loud. I felt his cock spasm, and a second later he was flooding my mouth with his thick, slippery, faintly bitter semen. I savored it, drinking every last drop, milking him until he became too sensitive to touch.

When he was finished, he smiled big. "Thanks!" he said, "Now I've got to get dressed, I'm running late for work."

I lay there naked on his futon, watching him get ready. In a way it was just as sexy to watch him get dressed as it was to watch him get naked. My finger kept sneaking down between my thighs, caressing my extremely wet and frustrated sex.

As soon as Jimmy was out the door, I masturbated myself to an explosive orgasm, right there on his bed. Three fingers of one hand were jammed up my pussy, the little finger penetrating my asshole; the forefinger of the other hand was a blur on my poor swollen clit. I came and came, convulsively, until the tears rolled down my cheek. By the time I was done, there was a big wet spot on his bed.


4.
He tried to mention it casually; he tried to be gentle about it. There was a girl at work, a girl his own age. They had been seeing each other. They were dating.

I knew what that meant and I tried not to let it hurt me. They were a couple. There could be no more jack-off games between me and Jimmy.

I didn't sleep well, and I was awoken from a frustrating and vaguely erotic dream. The living room light was on, I could see under the crack of my bedroom door, and I could hear voices out there.

Quiet as I could be on the creaky floorboards, I cracked the bedroom door.

She was skinny, and she had gorgeous red hair, and her tits were bigger than mine, the bitch. They were on full display because she, still in her black work pants, was kneeling in front of Jimmy, who was beautiful and naked, and she had a mouth full of his cock.

I could hear the little slurping noises she made, see his wet dick sliding in and out from between her lips, her freckled cheeks bulging with it, her large soft breasts jiggling with every move. His hand was caressing her curly red hair, he was softly encouraging her.

Then she stood up, letting his big wet dick swing free, and kissed him passionately on the lips. Her big tits mashed up against his bare chest.

My finger found my own clit, and my pussy was already slippery and drooling.

She stepped back from him and undid her pants. They fell to the floor, revealing long, slender legs and a pair of red thong panties.

They kissed a while more, as his hands roamed over her body, stroking her thighs, her tits, feeling up her tiny little ass. Then he hooked his thumbs around her panties and pulled them down in one smooth motion.

Her pussy was shaved bare, just like in the pornos. Her plump outer lips pouted sexily. I had a finger deep inside my pussy and it was making little squishing noises as I moved it in and out. I could smell their sex. Or maybe it was just my own.

He grabbed a condom from somewhere, ripped it open and rolled it down his pole.

I lost my view for a little while. They fell onto the futon bed together, and I couldn't really see what was going on. I could hear though, oh man could I hear!

While they fucked, I let my fingers do the walking. I was right on the edge. And then they changed positions. Jimmy maneuvered his girlfriend so that she was on her knees on the edge of the futon, bent over so that her head was resting on her hands on the floor, her tits hanging out and her pale little ass thrust up high.

He came at her from behind, fucking her hard, slapping her ass and making her boobs shake. She was loving it. "Oh yeah, Oh Jimmy, fuck me! Yes! Fuck me harder!"

His eyes were closed in concentration, his jaw was clenched. I was so fucking wet the girl-come was leaking out of me in long sticky strands. My clit felt like it was the size of a fucking tomato.

"You're gonna make me come Baby," she growled up at him, "Stick a finger up my asshole, please."

He slowed his pace down a hair, and very deliberately took his index finger and slipped it into his mouth like a little penis. I saw it glisten with saliva. He traced it down between the cleft of her buttocks. I saw her arch her back as his finger penetrated, and she rose up onto her hands and thrust back, matching him stroke for stroke.

Her red hair was a wild mop, her flushed tits shook and swung, her face (when I could see it) was a mask of ecstasy. She came loud and she came violently. If they had been in any way worried about waking me up, that was long forgotten.

She finally calmed down a little bit. Jim extracted his finger from her ass, placed his hands on her disgustingly petite hips, and started fucking her in earnest. I recognized the expression on his face.

"Come for me Jimmy, fuck my fucking cunt! Oh my God, I want you to come!" Redhead moaned up at him. She had a hand up between her legs, doing (I suspected) exactly the same thing I was doing at that exact moment.

I swear Jim was looking straight at me, staring right at my barely-cracked-open bedroom door. In one motion he pulled his raging cock out of her pussy, whipped off the condom, and grasped his penis in one strong hand, shouting something unintelligible and squirting come, white pearly come, all over Redhead's back.

I came at that instant like a dam breaking, chewing bruises into my forearm to keep from screaming out loud. I came like a slut, wagging my ass and grinding my clit in the safe enveloping darkness of my bedroom. When the spasms stopped, when I finished shaking, I extricated my sticky fingers and eased the door shut. I climbed into bed. But it was a long time before I could fall asleep.