Archive for October, 2011

Broken Up

Our break-up sex was stellar, ferocious, furious, better than any sex we’d had in months. It was so hot it was almost worth the splitting up.

Claudia bit my lips hard and pulled and twisted my nipples until I cried out and tried to pull away. She slapped me across the face and shoved me down on the bed.

She straddled my chest, facing my feet so I couldn’t see anything but her glorious ass. She hawked and spat on my pussy; smeared my juices and her spit all up and down my vulva; and then proceeded to brutally finger-fuck me.

She crammed four fingers up my wet cunt, and fucked me hard, jamming her fingers in and out and grinding her palm against my clit and chanting rhythmically as she fucked me: “Fucking whore! Fucking slut! Spoiled bitch! Stuck-up little cunt!”

Just before I came, she yanked her fingers out of my pussy, leaving me empty and drooling. She flipped me over onto my stomach, shoved my face hard into a pillow, and fucked my ass with multiple fingers, slick with my own juice.

I came hard, my whole body shaking, sobbing into the pillow as I shook and shuddered. Then she left me there, wet with tears and sweat and come, all alone and quivering on the bed like a big lump of jelly.

That was when I left. I needed to be someplace else. I needed to be in a city I’d never been in before, a place where I could walk down the street or go into a bar and not wonder if I was going to run into someone I knew. Fuck it: my royalty checks, such as they were, got direct deposited. Fuck it. Eyes red and teary and blurred, I threw together a quick bag: a change of clothes, a couple spare pairs of panties, my vibrator, my laptop; I left the apartment keys in the lock and walked down the stairs and out onto the sidewalk, and I headed to the A-train to JFK.

On my way to the subway, I threw my cell phone under the wheels of the caravan of taxicabs parading up 8th avenue. Fuck it, I never liked that cell phone anyway.

I hadn’t showered. I reeked of sex, and my cunt was squishy between my legs, and I felt shaky and unreal. I got myself on the redeye to SeaTac, and mercifully got an entire row to myself. I drank airplane vodka with trembling hands, and slept my way across the flat part of the country, and didn’t wake up until the wheels hit the tarmac.

The taxi driver was beautiful, a wispy, ethereal Pakistani guy about my own age with a pleasant, lilting accent and a hook nose that might have looked cruel on another face, but somehow came across as ironic on his. He was friendly and talkative, which normally drives me crazy, but that grey morning I really didn’t mind. It turns out he was a singer/songwriter, when he wasn’t driving a cab; he invited me to his next show. I would have totally done him, right there, blown him in the back of his cab, if he had just hit on me a tiny bit. I was in that kind of a mood.

Hanif dropped me off in downtown Tacoma, a city I’d never been to before. It seemed grey, grimy and grim and industrial. I paid him off, tipped him generously, and he gave me a flyer for his show. Then he drove away, leaving me blinking and disoriented in the overcast Northwestern morning light. It looked like rain.

The bars weren’t open yet, so I found a Starbucks. Over steaming hot, deeply overpriced coffee, I got on craigslist and started looking for someplace to stay.

Marcy was looking for a roommate. The price was right, and the address was within walking distance. I regretted, for a moment, tossing my cell phone. I’d have to get a new one. She responded to my email before I finished my third tall cup of coffee, and I said I’d be over in ten minutes. I took a piss and started walking.

When she answered the door, I knew I’d hit jackpot. Marcy was beautiful, and I wanted her right away. She was a little frumpy, in her mid- or late-thirties, an ex-punk rocker gone domestic. Her light brown hair was bleached blonde; she had tattoos, and a discrete ring in her nose. She was taller than me, and her breasts were bigger, and she wore a bathrobe that I was pretty sure she had nothing on underneath. She looked intelligent and rather jaded, a smart woman who knew better and did it anyway. I was in lust.

Her husband was an Army captain, on his third tour in Afghanistan. She was renting out the spare bedroom, for the extra money, and to keep her and her daughter company. It was a tiny room, with a view of an empty lot across the way, and occasional views of Mt. Rainier looming through the clouds behind. I took it.

She introduced me to her daughter. Blossom was a younger version of Marcy, with darker hair and solemn brown eyes. Her hair was chopped into a shaggy faux-hawk, and she wore a man’s red-checked flannel shirt and too much mascara and eye-liner. She hung back sullenly as Marcy introduced her, giving her mom the ‘I-am-going-to-murder-you’ look. You couldn’t pay me to live through that age again. No way.

I moved in. I got a new cell phone, and a new number. I drank too much and didn’t care. I lurked in my room and tried to write, starting a new story just about every morning, abandoning it by nightfall. I got intimately familiar with the Tacoma Mall, and with all the local bars.

Blossom was infatuated with New York. She was always bugging me for details of life in the city, and the fact that I was a published author seemed to elevate me to rock star status in her world. Which was all very complimentary; but also kind of annoying. I’d never been subjected to hero-worship before.

The house seemed oddly unlived in, more like a full-scale diorama than an actual home. It was too neat and tidy to be real. A photograph of the captain presided over the living room. He was handsome, a clean-cut version of a young Henry Rollins: a square jaw, and big, brown sensitive eyes. He looked kind but taut, a man of discipline. I bet he was a tiger in bed.

Marcy had a bad habit of wandering around the house in nothing but her bathrobe, and I developed a bad habit of following her around the house, perving on her and trying to catch a glimpse. Her boobs were large and bouncy, and looked delicious, and I was always hoping that one of them would slip out of her bathrobe, but it never did.

More than once, I accidentally/on purpose tried the bathroom door when I knew Marcy was in the shower, but she always kept it locked.

I went to see Hanif’s show. It was in a dark little café, no alcohol but very strong dark sweet coffee. The show was poorly attended; I may have been the only person who was there just to see him play. Hanif’s singing was hypnotic and soulful, a weird blend of middle-eastern and folk, whimsically political, like a Persian Arlo Guthrie.

He gave me a ride home in his taxi, and I sat in the front, and he wouldn’t let me pay for the ride. We parked in front of Marcy’s house and made out for a while. He was an amazing kisser. I liked his soft, brown skin. I liked his lips and his tongue. I liked his smell: sweet and spicy. I felt up his cock through his trousers. It was big and hard. I wanted to suck on it right then and there, but he gently pushed me away, saying thank you, but he wasn’t like that. He thanked me for coming out to see him play, squeezed me hand earnestly, and said that we should hang out again soon.

I went up to my room, horny and frustrated. When was the last time I had fooled around with a guy? College. Early college. I suddenly missed it: straightforward sex, penis-in-vagina action. It seemed satisfying and uncomplicated, like beer-and-pizza.

My vibrator wasn’t where I left it, in my underwear/sock drawer. It was lying out on the bed, as if someone had used it and left it there on purpose so I would know. I even imagined that it smelled faintly of pussy, not my pussy. I imagined Marcy lying on my bed, masturbating with my toy, fingers sliding in and out of her juicy pussy, vibrator pressed against her fat clitoris, her big boobs jiggling with every movement. I imagined licking Marcy’s pussy, teasing her and tasting her with my tongue, while Hanif took me from behind, agonizingly slowly inserting his long hard dick into my hungry pussy.

I came hard, flat on my stomach with the humming tip of the vibe pressed against my clit, and one finger halfway up my asshole, imagining licking Marcy’s wet pussy while Harif fucked me, thinking about the noises they would make. I pictured Harif sliding his thumb up my ass just before he came, shooting off inside me with a tortured howl, and that is what set me off. I shuddered and gasped through a long, drawn-out orgasm, and fell asleep, naked on the sheets.

I woke up early the next morning, fuzzy-headed and uncharacteristically non-hung over. I took my towel and went to the bathroom, but someone was already in the shower. I tried the door anyway and it swung open.

Marcy wasn’t in the shower, but her daughter Blossom was. She looked surprised to see me, but she didn’t say anything. Her skin was pale, and she had a fluffy black bush of pubic hair and dark little nipples on her small, tender breasts, and I could go to jail for even thinking what I was thinking. Tall and skinny, she didn’t have a lot of curves; her body was much more girl than woman. I excused myself and sat down on the toilet and peed. She didn’t close the shower curtain, and when she turned around, I had a fine view of her shapely little butt. I am definitely going to hell for the things I thought about that butt.

I made a serious pass at Marcy that night. I came home a little drunk after abandoning a frustrating day of ineffective writing, and found Marcy home alone drinking red wine. Blossom was off hanging out with friends, and I helped Marcy finish the bottle.

We were talking and flirting and she was wearing these faded old jeans with the knees blown out, and I kept catching glimpses of her pink panties down the gap of the back whenever she leaned forward to refill her glass, and she was wearing a tight Dead Kennedys t-shirt that showed off every detail of her magnificent big round breasts, and I kept imagining peeling that shirt off over her head and squeezing her beautiful ass in both hands and sucking those prominent nipples into my mouth, and I kept getting hornier and hornier and wetter and more frustrated, and finally, near the bottom of the bottle, I broke down and told her that I was really attracted to her.

She told me she knew, and that she was really attracted to me too, and she put her hand on my knee, and I realized that my panties were soaked all the way through and moistening my pants.

I clumsily put my arm around her shoulders and leaned in to kiss her, and she gently pushed me away. She said she was married. She said her husband would kill her. She said he’d divorce her if he ever found out.

Maybe we could do a threesome when he comes back. I was grasping at straws. She smiled ruefully and shook her head ‘No’.

I couldn’t sleep that night. I lay in the dark in my bed, the afternoon drunk gradually wearing off, the room slowly revolving on two axes. I masturbated until my pussy was sore and my clit was too tender to touch, and eventually passed out and dreamed frustrating and confusing sexual dreams.

The next morning, Blossom hovered over me as I ingested my first cup of coffee of the day, bugging me for details of life in the East Village. I wasn’t really in the mood for it, and answered her questions with grunts and monosyllables. I was hung-over, achingly horny and unsatisfied, and stung from being spurned by her hot but moral mother. It was a school day, and Blossom was wearing a lumberjack’s flannel shirt and a black studded leather choker around her neck that looked disturbingly sexy on her pale, slender throat.

I felt kind of bad, blowing her off, but Blossom eventually got the hint that I didn’t feel like chatting, and left me alone, and I made more coffee and locked myself in the bedroom and tried to write, but the words just wouldn’t come. I kept picturing Blossom on my bedroom floor, naked except for that black leather collar, tied and bound and helpless, with me towering gloating above her. I am going to burn in hell.

Two nights later, a little drunk and horny, but mostly just horny, I let myself into Marcy’s room after we had all gone to bed. The lights were off. Marcy always slept in the nude, she’d told me that before in a flirtatious sort of way; and when I slipped under the covers next to her, she was in fact bare-ass naked.

She was not asleep. She made a little Mmm-Mmm noise and snuggled up against me as I spooned her, pressing her wide, ample rump against my crotch.

I reached around and cupped one large, soft, warm breast in my hand, craning my neck around her neck to kiss her lips. She responded eagerly. I felt her nipple stiffen against my palm. Our tongues danced in the darkness, our mouths open and our lips pressed together.

Squeezing her breast tight, I slid one hand down between her thick thighs. There was a soft pelt of fur down there, and when my fingers parted her slit, she was very wet. I ran my index finger up and down her vulva, delighting in her folds, navigating my way up and across the slippery nubbin of her clitoris. Marcy sighed eloquently, arching her back and pressing back hard against me. My eyes were adjusting to the dim light of the bedroom, and I could just make out the tattoo across her shoulder blades: a busty blonde cowgirl on horseback herding cattle.

I slid down her body, pulling the sheets back with me, opening her ass-cheeks like a book. I could smell her excitement. Her butt was firm, wide, and hot. She had a tiny, tightly crinkled little anus; I was almost certain she was a virgin back there. I longed to sodomize her, jam my slick fingers up her anus until she whined and whimpered for mercy; butt fuck her so hard and deep that she wouldn’t know what had hit her. Restraint. I licked up and down the inside of those soft pale cheeks, avoiding her drooling pussy, avoiding her musky little asshole for the moment. She sighed and wiggled in response, straining back against my probing tongue.

She jumped when the tip of my tongue made contact with her anus. I drilled at that little hole, burrowing my tongue up inside her ass, working my way deeper and deeper. The taste was intoxicating. I let my hand find her pussy again. She was drenched, slippery wetness oozing out and running down her thighs. I slid two fingers up her hot, wet cunt, and pressed my thumb up against the swollen knob of her clitoris and furiously tongued her anus, shoving my face deeply between her butt cheeks, licking her asshole with everything I had, craning my tongue until it ached.

Marcy came, sobbing and shaking, and I stayed with her all the way through it though I couldn’t breathe. Her orgasm seemed to go on forever, the aftershocks pulsing through her body, making her shiver and quake again and again. Finally I extracted myself. I was covered in her come: my fingers were coated in it, my face was all wet. I got out of bed, retrieved my night clothes from where they had landed on the floor, and slipped quietly out of the room.

I was woken up early the next morning, far earlier than I was accustomed to waking, by the sensation of someone licking my pussy. At first I thought it was a dream, and it may have started out as one, but as I slowly gained consciousness, the sensation became more and more real. Whatever was going on down there felt nice, really nice, but it was frustrating. It felt like I was being licked by a puppy dog: eager and enthusiastic, but totally indiscriminate.

I blinked my eyes lazily open, and saw Blossom, naked but for a pair of baby-blue panties, sprawled out across my bed, her faux-hawk a shaggy mess, her pretty young face buried between my thighs. She was licking my pussy the way a cat might lap at a bowl of melting ice cream.

I spread my legs wide to accommodate her efforts, and she paused, looking up and grinning shyly at me, her big brown eyes sparkling with mischief. I couldn’t believe how young she looked from that perspective, but I certainly wasn’t about to stop her. Multiple gold earrings flashed in the early morning light as she dove back in, and I parted my labia for her, guiding her eagerly searching tongue toward my aching, swollen, horny clit.

When she found the spot, she knew exactly what to do, increasing her tempo and flicking her tongue up, down, around and around, bringing me rapidly toward the brink. I found myself raising my hips up to meet her, gasping for breath, straining up toward her. I took her small hand in mine and pressed it clumsily between my ass cheeks, willing her to take a hint and fuck my asshole. She took the hint, a little tentatively, inserting the tip of one finger into my hungry anus as her thumb slipped up my gasping pussy and her tongue continued its erotic dance on my clit. I came, the orgasm washing over me like a tsunami, groaning out loud, reveling in the sensations. It went on and on and seemed like it was never going to stop.

At last she extracted her various digits, and came up smiling, asking me if she’d done ok. I assured her that she had. Her young breasts were pink and excited. I asked her if she’d mind taking off her panties, and she did, almost shyly, sliding them off and exposing the soft, sparse bush of black hair that covered her little pussy.

I licked her pussy. She was sweet and wet and super sensitive down there. The lips were petite, her clitoris was tiny and shy, and she flinched away every time my tongue came close to it. I tried inserting a finger gently up her vagina, but it was too small and tight, and she whimpered like a scared kitten when I pressed, so I withdrew and concentrated on dragging my tongue lightly up and down the moist, pouting seam of her pussy, which she seemed to appreciate greatly.

We ended up with her bent over the bed, her face buried in the pillows, me licking her pussy from behind. I was deeply tempted to go for her cute little winking asshole, but somehow I restrained myself, limiting my debauchery to squeezing her sassy boyish ass-cheeks hard as I dragged the flat of my tongue up and down her vulva. While I did that, she masturbated, grinding herself against her own fist, and she came silently, her body tensing suddenly and shaking as if she were caught in a bout of violent hiccups.

Blossom left me then, grinning naughtily with her panties in one hand as she pranced out of the bedroom. She had to get ready for school. I could already hear her mother stirring downstairs.

I felt a little guilty, but not very. I knew I was a hopeless pervert, but I couldn’t bring myself to feel bad about it. Instead I rolled over, groped for my vibrator, and masturbated to what had just happened, coming deep and softly, and slipping back asleep and sleeping late.

When I got home that evening, half-loaded from an unusually productive afternoon of drinking and writing, Marcy met me at the front door.

Her husband was getting rotated home, she told me. It would be best if I found somewhere else to live. Her voice was strange and her mouth flapped open and closed like a ventriloquist’s dummy.

I gathered up my things, packed my bag, and called Hanif for a ride. He said he’d pick me up in twenty minutes. I sat in the shadow of a decrepit Dairy Queen on Pearl Street and waited. I thought about Marcy and her straight-as-a-ruler husband, I wondered if the sex they had was good. I thought about Blossom, imagined spanking her petite little ass till my hand stung and the welts rose red on her tender cheeks. I imagined her kneeling in front of me, wrists cuffed behind her back. I pictured myself fucking her with a buzzing toy while I choked her with my hand, my fingers wrapped around her delicate throat as she gazed up into my eyes, pulling my vibrator out of her cunt every time I let her breathe. I wondered when she’d lose her virginity and to who; I wondered if she’d ever think of me when she was grown-up and married. I thought about Claudia; wondered if she ever thought about me, wondered if she ever worried about me or wondered where I’d gone. I wondered if she was sorry for any of the things she’d said.

Hanif showed up in his cab, and I climbed in front next to him. He asked me where to, and I told him the airport. He told me that his boyfriend wasn’t home, and if I wanted to I could come over to his apartment and hang out for a while. I told him no, just SeaTac please, and he smiled at me in a sheepish and understanding way and pressed his hand warmly on my thigh.

We pulled out onto heavy traffic on I-5 north under a troubled sky heavy with low, dark clouds.


Comments (6)

Too Much of a Good Thing

‘Looking for a rideshare to San Fran. Can leave any time. Will split gas and tolls.’

I posted it the old-fashioned way, with a thumbtack on an old-fashioned bulletin board, because I’m an old-fashioned kind of guy.

Within a week, I got a response. Alyssa was driving across the country and wanted company. She sent me an email with a barrage of questions, some of which were pretty personal, and a lot of which seemed totally irrelevant; and she asked me to include a picture with my answers. I filled out her questionnaire and sent her a photo of myself; a couple hours later she said I’d do. She told me she was planning on taking her time, staying off the major roads as much as possible, making the coast-to-coast journey in a week or ten days or so. That was fine by me. She sounded cute. I figured I’d just hit the jackpot.

I met her on 8th avenue, over by the Port Authority, my overstuffed backpack slung over my shoulder. She was driving a little brown Honda that looked like it had seen better days.

“Get in” she said, and grinned, showing off two rows of perfect, sharp little teeth. She had frizzy brown hair, speckled with grey, freckles on her cheeks, and little crow’s feet in the corners or her eyes that showed whenever she smiled.

I got in. Alyssa must have stood a full head shorter than me, but she radiated a ferocious energy, like a pretty wolverine. I wouldn’t have wanted to tangle with her. All her features seemed to be sharp and pointy, and her slate blue eyes flashed dangerously in the morning sunlight. She was older than me, it’s hard to say how much, I’m lousy at that; at least ten years, maybe more. I sat down in the passenger seat next to her and buckled up as she pulled out into traffic.

There wasn’t much small talk as she deftly maneuvered the little car through the crowded corridors of midtown; traffic was heavy. As we inched our way toward the entrance to the Lincoln Tunnel, she placed her right hand lightly but decisively on my thigh. Inside my jeans, my cock snapped rigidly to attention.

Well. This was certainly going to be an interesting car trip.

By the time we emerged into New Jersey, Alyssa had fished my dick out of my pants, and was happily playing with my cock, petting it like a playful puppy.

“Why don’t you take off your jeans, Boy-O?” she said, “They’re only getting in the way.”

I was happy to comply, kicking off my pants and my underwear, sitting nude from the waist down as we sped along the Jersey Turnpike, my cock pointing eagerly up like a flagpole.

“Much better,” Alyssa said, and smiled sweetly. She set the cruise control at 65, and got down to the serious business of jerking me off, her thumb and forefinger wrapped around my erection, stroking constantly, sometimes fast and sometimes slow; sometimes squeezing me tight and sometimes barely touching my aching flesh.

“Let me know before you come.” she told me, and after fifteen or twenty minutes of exquisite torture, I yelped out that I was about to blow.

“Here, take the wheel!” she commanded, and before I could protest, she had dropped her head into my lap, opened up her thin red lips, and swallowed the top half of my cock whole, cupping my balls tightly with one  hand while she deftly jerked me off with the other.

I managed to keep the car on the road, though I swerved like a drunk all over three lanes of traffic as I came, lifting my ass up off the seat and pumping what seemed like gallon after gallon of semen into her incessantly sucking, insatiable mouth. She stayed with me all the way through, swallowing every drop of my come and leaving my dick wet, soft, and tired.

Finally she came back up for air, taking the steering wheel back from my shaking hands.

“Mmmm. Oh yeah Boy-O, that was delicious. I’ll never get tired of that stuff! No, leave your pants off. I like you better that way. I’m married, by the way. I hope that isn’t a problem for you.”

I hadn’t noticed the gold ring on her finger before. It wasn’t a problem for me.

She chose an exit, seemingly at random, and we pulled off the interstate and onto the rolling back roads of Pennsylvania farm country. As we drove, she toyed idly with my dick, which slowly rose back into a state of erect excitement.

“Not bad, not bad at all.” she said, “Why don’t we stop right here?”

We pulled off at a wide place in the road next to a farmer’s fields. Brown cows watched us incuriously as we got out of the car and stretched our legs. I sat on the trunk and Alyssa bent over and started giving me an expert blowjob.

“Don’t hold back,” she said, “we’ve got plenty more driving to do. Would this help?” She pulled up her top and unsnapped her bra, exposing a pert pair of smallish, lightly freckled breasts with pink, pointy nipples. They jiggled nicely every time she moved.

A semi-truck blew by and honked his horn appreciatively. Alyssa buried her face in my crotch, swallowing most of my dick, bobbing up and down on me and swirling her tongue round and around my shaft, licking the ridges of my head and slurping at the underside. It didn’t take me too long before I was humping back at her pretty face, fucking her mouth, coming once again, moaning and shouting out loud in the warm open air, filling her mouth with my semen.

We got back on the road, making our way along lazy country roads, sometimes making wrong turns and having to backtrack; but generally heading south and west. Alyssa had me strip nude in the passenger seat next to her. She said I looked cute that way. She let me put a t-shirt on when we stopped for gas, and I got fully dressed when we stopped for lunch at a greasy-spoon diner in the middle of nowhere. She didn’t ask me to pay for either the gas or the food, and I didn’t offer.

She played with my cock and balls from time to time as we drove. It seemed to amuse her no end to make me hard and then to watch me wilt all over again.

Our first day’s drive ended at a hotel somewhere outside of Parkersburg. It was a way nicer hotel than I would have picked, but then again, I hadn’t paid for any of the gas or tolls, and Alyssa had bought me lunch. I half-expected her to get a room for the both of us, but she got her own room, and I ponied up the credit card and got a room for myself. We got our stuff our of Alyssa’s decrepit Honda, and then we went our separate ways.

I took a very hot shower and ordered a pizza and sat on my bed, watching stupid tv and feeling kind of numb. It had been quite a day, a lot of driving, and a lot of stimulations, and I felt a little bit shell-shocked.

There was a knock on my door. It was Alyssa, in a blue denim dress. She sat on the edge of the bed, and I gave her a foot massage for the better part of an hour while she chatted with her husband on the phone. That’s a long time to rub someone’s feet, and my hands started to get tired, but every time I started to think about quitting, Alyssa gave me a sharp look that made me change my mind and got me right back on task.

Every now and then, as I massaged her petite feet, I’d catch a glimpse of her skimpy green panties up her skirt. Toward the end of the conversation, she hiked up her dress, and slid her fingers up underneath her panties. Inside my pants, my cock was straining hard.

Finally, she hung up the phone. “Why are you not naked yet?” she asked.

I hurriedly got undressed as she pulled off her blue dress and stripped out of her bra and panties. She had a lovely, taut little body, with a mostly flat tummy, curvaceous hips, and short but thick, almost stubby thighs. Her breasts seemed perfect for her frame, small and pert; and her pussy was crowned with a neat little triangle of dark, curly hair. She lay back on the bed, spreading her legs wide, opening her pussy with two fingers. The inner lips were delicate-looking, small, pink, and wet.

“Saddle up, Cowboy!”

Feeling kind of awkward, I rolled on a condom and climbed on top of her, slipping my erection straight up her eagerly salivating hole.

She was shockingly hot inside, tight, wet, and slippery. Her pussy felt amazing on my cock. Right away she grabbed my ass with both hands and pulled me deeper inside.

“Fuck me! Fuck me hard, Boy-O! Harder!”

I complied, fucking her little pussy with a vengeance, as hard and as deep as I was able. She loved it, bucking back against every stroke, her hands on my ass cheeks pulling me insistently deeper, hissing encouragement through clenched teeth. In other circumstances, I would have had to fight to not come right away; but since I had already gotten off twice already that day (three times if you counted my late night/early morning masturbation session), I was in no danger of shooting off early.

“Harder! Faster! Harder, damn you, harder!” She was writhing underneath me, squirming and wiggling, arching her back and lolling her neck from side to side, every muscle in her face clenched. I knew she was right on the edge. Breathing hard, my heart pounding inside my chest, I complied, fucking her with everything I had, until my muscles were quivering and sweat was running down my face.

When she came, it was a beautiful sight. She threw her head back, and her whole chest flushed mottled red. I could feel her pussy spasmodically squeezing my cock, her abdomen shook as every muscle clenched and relaxed, and she screamed loud enough to let everyone in that hotel know exactly how good her orgasm felt.

I was glowing. I felt like I had just run a 10k, and fast. I fucked her a little more, but we were both pretty exhausted, so I ended up pulling out and removing the condom and jerking off into her open mouth, which she seemed to appreciate.

Then she got dressed and went back to her own room, leaving me to my tv and my congealing pizza. I crashed out hard, and didn’t dream.

We hit the road the next morning, nice and early, right after breakfast. Alyssa was all smiley and cheerful and chipper. The character of the land had changed, we were in distinctly Midwestern territory now, driving past farmland that seemed to go on for miles, interspersed with colonies of McMansions, sprouting up like toadstools.

“Come on Boy-O,” Alyssa said, “You know how I like to see you. Nude and lewd. Lose the clothes.”

I dutifully stripped, and Alyssa reached right over and started squeezing my dick.

“Are you serious?” I asked, “Again? Already?”

She raised an arch eyebrow at me. “You’re not complaining are you Boy-O? ‘Cause you can always get out and start walking.”

I wasn’t complaining. And soon enough my dick was bobbing merrily up and down, hard as a dry stick, and I was squirming in the seat as her hand pumped up and down.

She had me take the wheel while she blew me for a while, but thought her mouth was talented, and it felt glorious, she wasn’t able to make me come that way. So she pulled the car off onto the shoulder and had me get out and stand behind the door as she knelt in front of me, licking my balls and working her tongue up between my butt cheeks as she jerked me off. It took a little while, but she knew what she was doing, and the orgasm was well worth the wait. Her hand was a blur, and her tongue was brushing up against my asshole, and I finally came, spattering semen into her waiting palm. She licked it all up, like a hungry cat, and we resumed our drive.

After lunch, in the parking lot of some small-town diner, she climbed into the back seat and pulled down her pants. She told me to jerk off onto her pussy while she masturbated, and I did, crouched in front of her crotch, pumping my own cock hard and fast as she fingered her pink little clit. I kept having visions of a small-town sheriff tapping on the window, and that motivated me to get off as quickly as I could. Seeing my pearly-white come splashing on her pouting pussy lips seemed to set her off, and she came with a long, drawn-out yawning groan and a satisfied smirk.

Another hotel, once again outside of my price range, but since I wasn’t paying for gas, I figured it kind of equaled out. I rubbed her shoulders while she talked to her husband on the phone, and then she went down on me. Nothing happened. I was kind of mortified; I wasn’t used to getting anything like this much attention, but still, I had always been up and ready for any action that came my way.

Alyssa didn’t appear to be too concerned. If anything, she seemed mildly annoyed, as if her car had developed a minor mechanical problem that would necessitate an unplanned stop. New wiper blades, for instance.

She had me lay on my back on the hotel bed, and licked my body all over, starting with my neck, pausing at my nipples, and working her way down from there. My dick stayed stubbornly soft as she licked it like a big wet noodle. She nudged my thighs apart, licking and sucking my balls exquisitely, and then pushed my knees back and started licking my ass, dragging her tongue up and down my crack, pressing her tongue against my anus.

It felt amazing, and I started to feel a tell-tale tingling in my cock. She was fingering her pussy as she licked my asshole, and it was almost too sexy for words. Then, without so much as a by-your-leave, she slipped a wet finger straight up my ass.

I yelped, and she giggled. It didn’t hurt. It felt weird. She was moving her finger around in there, making little beckoning motions. If it wasn’t exactly pleasurable, it certainly wasn’t unpleasant either. And my cock responded right away, rising tall and stiff, like a circus tent pole.

She withdrew her invading finger, leaving me feeling tingly and hollow; tossed me a condom, and climbed on board for the ride. She bounced up and down on my dick, grinding her pubes against mine until she came. Then she clambered off, removed the condom, and told me to masturbate into her mouth. I dutifully did as I was told, but I just couldn’t bring myself off. I whacked off until my toes curled and my ass cramped, but I couldn’t quite push myself past the threshold. Eventually she left me there in the hotel room, hard, sore, and frustrated.

We were worming our way into the American Heartland, long stretches of two-lane back road winding through industrial-sized fields of soy, wheat, and corn. I sat naked next to her as she drove, leaning back in the seat and enjoying my morning hand/blow job. Once again, I came in her mouth, and once again she slurped it all up and wrung me out like a damp sponge.

It was a frustrating day of driving; construction, wrong turns, backtracking, and pokey local traffic. Several times I offered to take a turn behind the wheel, but Alyssa curtly turned me down.

“It’s my damn car, and I’ll do the driving, thank you. Your job, Boy-O, is to sit there and look good.”

So I did. She played with my dick on and off all day, sometimes even handing me the wheel and having me steer for a while she sucked on me for a few miles, but never bringing me to orgasm, or anywhere even close. At one point we pulled off the road, and she had me fuck her face, holding the back of her head and jamming my cock down her throat until she choked and coughed, but I still couldn’t come, which seemed to annoy her.

We seemed to have ended up in the absolute middle of nowheresville. It was one giant strip mall, with plenty of Wallmarts, used car dealerships, and hot-tub outlets, but not a decent hotel to be found. It was getting dark before Alyssa finally settled on a dingy-looking Motel 6. She may not have been thrilled about the place, but I wasn’t complaining. This joint was much more in line with my own personal budget.

After checking in, we each made our own separate way over to the bar that shared a parking lot with our motel. I took a corner table and ordered a beer and started reading one of the books I had brought along, a Jack Kerouac road-trip novel. It was the first time I had so much as opened a book the whole journey.

As I sipped my beer, I observed Alyssa in action over at the bar, chatting up one of the locals. The object of her flirtation was a heavy-set blonde guy in a grey suit, who looked like he might sell tractor tires for a living. I felt an odd mixture of jealousy and relief as I watched her put the moves on him. She was, of course, free to do as she pleased; and frankly I could use the break.

It was after midnight when Alyssa rapped on my door. She smelled of whiskey and cigarette smoke, and her curly mop of hair was wayward and disheveled. She pushed her way into the room, rubbing her body against mine.

“He had a pretty big dick,” she said, “but he had no idea how to use it. Oaf. Pretty useless. He lasted all of about thirty seconds. I didn’t even get to taste a single drop.” She added petulantly.

Alyssa shrugged off her floral summer dress, which cascaded into a heap around her ankles. She wasn’t wearing anything underneath. She lay down on her back on my bed and spread her legs wide apart, and I got down between her thick, stumpy thighs and started licking her pussy.

She was very wet, salty and musky and delicious. Her pussy was freshly fucked, relaxed and open and squishy. I really enjoyed going down on her, dragging my tongue up and down her vulva, nibbling at her lips, flicking my tongue at her erect little clit. She seemed to enjoy it too, rubbing back against my face and making appreciative noises; but all too soon she pulled away from me.

“Thank you, that was nice,” she said, “But I really need to feel you inside me. Not my pussy; it’s too tender right now. Fuck my ass.”

It was not an invitation I’d ever received before, though it was something I’d always wanted to try. She rolled over and got on her hands and knees on the bed, her rump thrust lewdly up in the air.

“Do you have any lube?” I asked dumbly, my cock sticking straight out from my crotch like the bowsprit of a sailing ship.

“Use spit,” Alyssa told me, “That’ll work, if you use a lot of it.”

I stuck my face between her pretty ass-cheeks and started licking.

Her asshole was a tiny little button, crinkled and tight. I teased it with the tip of my tongue, eliciting a throaty sigh and a groan. She tasted clean and earthy. I lapped at her ass with the flat of my tongue, spreading spit all over back there as she fingered herself. Her juice mixed with my saliva, and I drilled my tongue up into her anus. I was getting really into it when she interrupted me.

“That should do it, Boy-O. Fuck my ass now.”

I repositioned myself and took careful aim. I wasn’t sure how my dick was going to fit into that teensy little hole. I pressed the bulbous red head of my cock against her tiny asshole, and carefully nudged forward. Amazingly, she opened right up and accepted my dick. The head of my cock slid right up inside her and she grunted.

She was tight, insanely tight. It was like trying to fuck a clenched fist. Her sphincter muscles formed a ring, squeezing my shaft as my dick invaded her ass, slipping gradually deeper and deeper up her butt.

“Don’t… be… so… uh… fucking gentle!” she growled at me through clenched teeth, wiggling her ass and pressing back hard against me.

I started fucking her ass in earnest, abandoning myself to the pleasure of it, casting off all restraint. She grunted with each thrust as if she were getting punched in the gut. Her fingers were squishing loudly between her legs as she masturbated furiously.

I wasn’t going to be able to last much longer, and I started fucking her ass hard and deep, howling out loud, and she joined me, baying like a she-wolf. She came, her entire body going rigid underneath me, and that set me off. I slammed into her one last time, my cock twitching and pumping hot sticky semen straight up her butt. Then I collapsed on top of her, and we lay there for a while, breathing hard, our hot, sweaty flesh pressed together, my soft, leaking cock captured by her ass.

“Thanks,” she said at last, “I needed that.”

She extracted herself and pulled on her sundress, and left me lying there, a tired and sweaty-sticky heap.

I slept hard that night.

Alyssa woke me up early the next morning, looking to take advantage of my morning wood. She climbed naked into bed with me, and had me straddle her chest and rub my dick between her tits while she masturbated. It felt nice, and it looked incredibly sexy, my hard cock sliding up and down between her perky, freckled tits, while she craned her neck down for a lick or two, her fingers busily strumming between her legs.

Then, without warning, she jammed a finger (or two!) up my asshole, all the way up to the knuckles. I jumped and yelped, and suddenly I was coming, squirting all over her chest and neck and tits. It actually hurt when I came, as if Alyssa was making lemonade, and I was an used-up lemon that she was wringing every last drop of juice from.

She laughed merrily and wiped up my splattered semen with her finger and licked her finger clean, and we got dressed and had breakfast and hit the road.

She played with my cock in the car, but I stayed persistently soft, even when she took me in her mouth and sucked on me like a strand of spaghetti, swirling her tongue all around the crown, and even reaching underneath me and tickling my asshole.

“Are we going to have to put you on the little blue pills?” she asked crossly.

My dick was tender and a little raw from all the fucking and sucking, and my balls ached, a deep-down worn-out ache.

“Can we just give it a little rest?” I asked, “I’m not a dildo. I’m not your own personal sex toy.”

She swerved to the side of the road, stomping on the brakes hard enough to make as skid a little on the gravel shoulder.

“Was that a complaint? Are you complaining, Boy-O?”

Without a word, I gathered up my clothes and took my backpack and climbed out of the car, feeling her slate-blue eyes burning into my flesh like James Bond lasers. As soon as I was out, she slammed the Honda into drive and pulled away with squealing tires, disappearing after a few seconds over a low hill up ahead, the sound of her engine slowy fading away.

Feeling shaky and rattly, like a dried-out husk blowing in the wind, I got dressed a few steps into the field, surrounded by a dense forest of cornstalks that loomed taller than me. Stepping back onto the side of the road, I shouldered my backpack and started to walk.


Comments (1)

Taken For a Ride

I knew from the start that it must be a put-on. I was a high-school nerd-girl; short and chunky and bookish and rather shy, a dweeb and a geek and a sexually frustrated more-or-less virgin. Vince was thirty-something, with a fancy car, a receding hairline, a wedding ring, and the body of an ex-competitive swimmer not yet gone completely to seed. He had to be taking me for a ride. So I went along for the ride with him.

He picked me up after school. He didn’t want to pick me up right at my school, because he didn’t want people to see me getting into some strange dude’s car, and he didn’t want to pick me up at home for the same reason. So he met me in front of the post office, a couple blocks down the street. It was all pretty sketch.

He drove a little black sports car. I don’t really pay attention to that kind of thing, but it looked expensive. When I asked him what he did for a living, he said he was an investor.

We drove for quite a while, and about ten minutes into the ride, he casually slid his hand over past the stick shift, and rested it on the exposed naked skin of my thigh. Despite myself, I felt my pussy getting all gushy wet and horny under my stretchy black cotton skirt. I don’t wear skirts very often, and I hoped this one didn’t make my butt look absolutely vast. I asked Vince if he was still married, and he said yeah, and asked if that was a problem for me. I said ‘No’, and it really wasn’t, and I didn’t ask him any more questions.

We had dinner at a tiny, dark, fancy, expensive Italian restaurant. Vince ordered for me, which was kind of annoying, but the food was delicious. He also ordered me a glass of wine, which the waiter brought without any comment about my age. I didn’t mind the taste, not at all, and it quickly made me a little light-headed and giggly.

Conversation was stilted; when it came right down to it, Vince and I didn’t really have much of anything in common. The copious amounts of homemade Italian food helped fill the awkward gaps. He kept running his hand up and down my thigh under the table, which kept my pussy juicy and squishy all through the meal, my clit obnoxiously pert underneath my panties.

We went back to the car, and he opened the door for me. I was pleasantly nervous and tipsy from the big glass of red wine I’d drunk. It was dark in this part of town, there weren’t any street lights, and it was starting to rain. I was all trembly with anticipation.

He got in beside me and closed the door, but didn’t start the engine. The dome light faded to black.

“Well, how about it?”

“How about what?” I asked. I knew exactly how about what, but I wanted to hear him say it.

“How about a little blowjob?” he asked. For the first time that night, he sounded just a tiny little bit vulnerable.

“Sure,” I said, putting on my best smile, “No problem.”

I actually didn’t have a lot in the way of experience at the time; I hadn’t attempted an actual blowjob in several years. The last time I’d gotten any genuine action had been with Karl. I still was a more-or-less a virgin. More-or-less, because the one and only time I’d been poised to have real, actual sex, three things had happened simultaneously:

1) Karl, my junior high school lab partner, fellow d&d enthusiast, and lately jerk-off partner, who’s basement it was that we had been fooling around in, had attempted to slip his stiff dick right up into my spread wide open, drooling, eager young virgin pussy;

2) Karl immediately orgasmed with a little choking squeal, pumping gob after gob of sticky white semen all over and around and up inside said pussy like a soft-serve dispenser gone haywire; and

3) Karl’s mom had walked in on us down in the basement and had started screaming and cursing at me and had chased me out of the house and banned me from ever seeing her son again.

I was of course, terrified that I’d gotten pregnant –pregnant and I didn’t even get laid!—but more than that I was bummed out that my one reliable source for sexual satisfaction had been taken away: Karl was moved to a different school, and I never saw him again. I got my period just fine, and resumed my steady but lonesome diet of porn and masturbation. I figured I’d just die a virgin. More-or-less.

Back to the present. Vince extracted his penis from his black slacks and tighty-whities. His cock wasn’t, as I had been a little afraid, intimidatingly enormous. It seemed like a nice sized cock, maybe a little on the small side, though I was basing that on very little real-world experience and a ton of porn. It was one of those funky dicks where the crown is smaller than the actual shaft, which was pale, and strained up and out, curved like a drawn bow. A glistening drop of precome was balanced on the tip, like a dewdrop on a spear of asparagus. I stuck out my tongue and licked it off.

And was momentarily blinded by the flash of his camera.

“What was that all about?” I asked.

“I just want something to remember this moment by.”

Yeah, right. I blinked a couple of times to get the dazzle out of my eyes, and then I got serious about sucking his dick.

I LOVE sucking cock, and while I hadn’t had much actual practice, I had watched an awful lot of blowjob videos with one hand on the mouse and one down the front of my panties, and I had spent a lot of time and energy daydreaming about just exactly how I would do it; so I didn’t think I would disapoint.

I started out just slurping the length, trailing my tongue along the underside of his rigid penis, kissing his balls and the petite scarlet crown; and then when he started to get really into it, I opened wide and swallowed. I admit it, I’d practiced on bananas before, and his cock wasn’t an especially big banana. I could get the whole thing in my mouth and keep it there, bobbing my head up and down and keeping my teeth well out of the way. I don’t know about him, but I was more or less in heaven.

He started to get really into it too, moaning and groaning and humping my face and calling me a horny bitch and a slutty little cunt. The more turned on he got, the hotter it was for me. His cock was swollen with excitement, trembling, practically pulsating. I could tell he was just about to come.

Right on cue, he yanked his slippery dick out of my mouth and started jerking off. It took about two seconds, and then he came, squirting his hot, sticky semen all over my face: into my eyes and hair, up my nose, across my cheeks and lips and chin. Again, the flashing camera. I smiled up at him as the shutter clicked again and again.

He tried, I guess I have to hand him that. After I had wiped up with a thoughtful handy Kleenex, he kissed me and squeezed and rubbed my breasts through my shirt, sliding his hand up under my skirt and fingering my pussy, which was admittedly, quite wet and slick by this point. But it just wasn’t working for me. Before I could even fake an orgasm, he gave up, withdrawing his sticky fingers and offering them up for me to lick off. Which I did, I might add, perfectly happily. More camera flashes. Then he zipped up, and stepped out of the car to smoke a cigarette in the drizzle.

While he was standing on the sidewalk smoking, I went through his wallet. There was his driver’s license, his credit cards, a fat wad of cash. I helped myself to a couple twenties. There was a picture in there of his wife and young child. They were both blonde, conventionally attractive, as if they were models for the Sears portrait studio. The kid looked to be about six; the mom wore too much mascara and had big hair and scary fingernails.

I put Vince’s wallet away and picked up the camera, flipped through the pictures he’d taken. The girl on the little LCD display looked pretty hot, I thought, mouth full of cock, come splattered all over her face. I felt oddly smug looking at those pornographic snapshots. I wondered what his wife would say if she ever saw them.

He drove me home, a long, silent ride. I don’t think a single word was spoken the whole drive.

“I’ll see you soon,” Vince said when he dropped me off up the street from my parent’s house. He didn’t kiss me, and I didn’t expect him to.

Three whole weeks, and he didn’t call, didn’t email, didn’t text. Despite myself I let it get to me. I brooded and obsessed and fretted. Was I not attractive enough for him? Didn’t I do a good job sucking his dick? Did he not like me?

Possibly surprisingly, I wasn’t worried about the pictures. Actually, there was a part of me that hoped that he’d posted them on the internet; that people would look at me and see a wild, sexy thing. Maybe some of the cute guys at school would jerk off to pictures of me sucking dick in a car. Maybe some of the prissy missies at school weren’t such prissies after all.

He texted me out of the blue, asked if I could ditch my afternoon classes. I responded ‘Of course’. He picked me up down the street from the school, in front of the post office.

We drove down to the reservoir and got high together, pre-rolled joints that looked like cigarettes. We kissed a lot and made out, and I groped him and found his cock nice and hard, and he groped me back. Then we drove back to his apartment.

His wife was at work, the kid was in school. He poured me a shot of vodka that made me choke and cough. We migrated inexorably into the bedroom.

I imagined that his wife had picked out the colors: the walls were avocado and the ceiling was pomegranate. There was a framed picture of the two of them together, atop the dresser. It might have been their senior prom; they both looked young, bright-eyed, All-American. They were smiling big and wide, showing off their perfect rows of white teeth. It might have been an advertisement for a high-end cosmetic dentist’s office.

Vince lifted me up and plopped me down on his bed, and then he lay down on top of me. We kissed and groped and fondled a bunch more, and then my shirt and my bra and then my jeans came off, one after the other. Vince sucked my nipples and played with my pussy until I was so drooling wet that the crotch of my panties was soaked through. His cock made a delicious looking tent in the front of his slacks, and I almost couldn’t wait to get my mouth wrapped around it. Almost.

“Would you mind?” I asked, feeling very shy and self-conscious about asking, “Would you mind going down on me a little bit?”

“Sure thing, Baby!” he said, “It would be a pleasure!” And he pulled off my soggy panties with a flourish.

I lay back on the sheets and spread my legs wide as he dove in. I was atremble with anticipation; no-one had ever done that to me yet, and from what I had read it was supposed to be orgasm-city.

Unfortunately, he didn’t seem to be very good at it, or maybe he wasn’t trying very hard. His tongue was excruciatingly clumsy, seeming to lick everywhere except the neediest parts. Which might have been ok if it had led in the end to sweet release, but he was only down there for about two minutes before he came up for air, beaming like a benevolent Santa Clause.

“How was that?” he asked, and I said “Thank You”, because I didn’t really know what else to say. And then the doorbell rang, and he got up and went to answer the door, still fully dressed, leaving me naked, wet, horny and frustrated on his marriage bed.

While he was out of the room, I did a quick bit of snooping. There was a bunch of fairly conventional ladies’ underwear in one of the top doors of the dresser; presumably his wife’s. In another one of the drawers was a glass pipe, a fat baggy of pot, a box of condoms, and chrome-plated egg-shaped vibrator. Sitting on top of the dresser, next to their prom night picture, was a dish with some spare change, a few paperclips, and a spare set of apartment keys. I lifted the keys and slipped them deep into my jeans pocket before resuming my position naked on the bed. I masturbated a little, because I wanted him to walk in and see me doing that, and to keep everything nice and wet down there, and because it felt nice.

I suppose I should have flipped out, or at least been discomfited when Vince walked back into the room with another man in tow, but between the pot and the vodka and the screamingly turned-on state of my vagina, I took it all in stride.

He introduced the new guy as his friend ‘Francis’. Francis was not someone I would normally think of as attractive at all. He looked to be about the same age as Vince, with a high forehead and hairy forearms and a bit of a belly and a greasy complexion. He smiled at me and shook my hand, big soft mitts that reminded me of warm Play-Doh.

The guys snorted a couple lines of coke off a mirror on the nightstand, but they didn’t offer me any. Which was ok, because I wasn’t sure I wanted to try that anyway. Then they both got naked and lay down side by side on the bed, and I went to town sucking their hard dicks, alternating between the two of them.

Francis’ cock wasn’t much longer than Vince’s, but it was notably thicker, and much hairier. I liked sucking Vince because it was easy to get the whole thing into my greedy mouth, and I didn’t get his hairs stuck in my teeth, but I really enjoyed sucking them both. The situation was hugely exciting, and I savored the strong, male taste in my mouth.

Then Vince got up and rolled on a condom and started fucking me from behind. It felt nice, and I was secure in the gleeful knowledge that I really and truly, without a doubt, was no longer a virgin. Francis grabbed Vince’s camera and started snapping pictures. He stood by the side of the bed and fed me his thick, hairy, strong-tasting cock while the shutter clicked away like a metronome.

Vince didn’t last very long. He slipped straight into overdrive, humping wildly away at me, his cock twitching inside the condom as he came inside my pussy, emitting a series of hiccupping, stuttering grunts as he came.

They traded off with the camera, and Francis maneuvered himself behind me. It took a little work to get his fat, condom-wrapped dick up my cunt, but Vince had limbered me up, and in the end it slipped right on in. He fucked me while Vince took pictures. His style of fucking reminded me of a steam locomotive: short, almost violent thrusts, starting out slow, and slowly chug-chugging into a fast, staccato rhythm.

I might have even come like that, he had me pretty close, but before I could slip over the precipice, he yanked his dick out of me, peeled off the condom, and with a deep, drawn-out, guttural growl, he shot off all over my back, splashing me with come from my butt-crack all the way up to my shoulder blades.

I collapsed onto the bed, a sweaty, panting mess. The two guys stood over me as I masturbated face down atop the sheets. They made small talk while I fingered myself, commenting on my body (‘horny little slut’ ‘look at that ass wiggle’ ‘fucking tight little pussy’) and snapping more pictures. I finally came, a long, deep orgasm that left me twitching, gasping into the bed linens.

We all got dressed, and Francis took off, and Vince gave me a ride back to school, which was just getting out. He told me he’d call me soon, within the next couple of days for sure. I got out of the car and mingled in with the kids streaming out toward the yellow busses. I was acutely aware of the smell of sex emanating from my body, the gooey wetness in my pussy, my damp panties, and his spare keys jingling in my pocket.

He didn’t call. A week passed. My period came and went. He still didn’t call, and I realized that he wasn’t going to.

I email him a couple of times, late at night, lonely and desperately horny. He never replied.

I was in a funk, and to get out of that funk, I decided to buy myself a toy. I walked down three concrete steps into an Adult Novelty Bookshop, up the street from the bus station. The place was lit with harsh fluorescents that cast no shadow. There were aisles and aisles of DVDs, every genre imaginable. I was the only female in the place, and distinctly underaged, and I felt acutely stared-at as I made my way to the back wall, where the sex toys were kept.

It seemed like all the vibrators were marketed toward men: the packaging was all images of impossibly busty, big-hair women with a lot of make-up, licking their fingers seductively and making eyes at the camera as they nibbled their plastic toys.

Regardless, I hurriedly picked one out, a sparkly pink model, realistically modeled to look like a fairly enormous penis. I brought it over to the cash register, paid for it, watched the clerk pack it carefully into a brown paper bag, then I rushed home to try my new acquisition out in the privacy of my own bedroom.

I was surprised to discover that the vibrating did absolutely nothing for me. It felt like an annoying buzzing, a quasi-tickle, that’s all. There was nothing erotic-feeling about it.

I tried sliding the toy up my pussy next. It was difficult and a little uncomfortable to get it in; apparently my eyes were a little bigger than my pussy. Once the oversized phallus was lodged in my cunt, I felt full, stretched out, somewhat obscene, but not particularly turned on.

It was when I pushed it up against my asshole that I hit pay dirt. The toy didn’t go up inside my butt, exactly, but when I got everything all nice and slippery, and shoved the head hard up against my anus, hard enough that I was stretched open to the point just before it started to hurt; and if I kept it wedged right there, and played with my clit in the normal way, the orgasms were positively explosive. Especially if I were watching filthy porn at the same time. The pressure seemed to make my whole vulva super-sensitive. It made my clitty strain outward. I could whack off for hours like that, just dancing little circles around my horny, swollen clit, the big pink dildo nestled tight up against my anus.

I met a boy. His name was Henry, and he was a year younger than me, and he sat beside me in Creative Writing. He was one of those guys who’d probably be really really hot if he had a little self-confidence. He habitually wore these awful brown-and-orange polo shirts, and jeans that were too big for him. The more I got to know him, the more I liked him, and the cuter he seemed to become.

Henry drew cartoons, and if he was shy about showing me his work (he hardly ever showed anyone his cartoons), he was painfully reticent about showing me his pornographic drawings. Once I’d seen one, though, I was insistent.

They were really good. He drew in pencil, lifelike drawings of people having sex, sex of every variety imaginable. Straight couples, gay guys, lesbians, Vikings, fairies, punk rockers, multi-tentacled space aliens. I spent an afternoon sitting on a beat-up old couch in his basement, going through his secret portfolio. Then I insisted that he draw me.

I gave him his first-ever blowjob on that disreputable old couch. He kept holding back, I guess he thought I wouldn’t want him to come in my mouth. I quickly disabused him of that notion.

Henry had a nice dick, large but not too big, and he kept it shaved clean, and he liked to wear girls underwear. I didn’t think much of that the first time I fished his erection out of a silky pair of purple string bikini panties, other than that it was sexy. I didn’t find out until much later about his penchant for cross-dressing, or his secret fascination with strap-ons.

Henry was also, and it made him blush to admit it, a bon-a-fide virgin. I promised to relieve him of that condition at the earliest possible opportunity. I even went on the pill so that he could come inside me and we wouldn’t have to fuck around with condoms.

We ditched school, and went giggling past the doorman into Vince’s building. I had all kinds of butterflies in my stomach as we took the elevator up to his floor. What if the key didn’t work? What if he was home? What if his wife was home?

The key fit perfectly, and the apartment was empty. There were light rose-pink sheets on the bed, which clashed horrendously with the walls and ceiling.

We got naked. I extracted Henry’s big, smooth, hard dick from the red g-string he was wearing, already drooling pre-come with eager anticipation. I started off by giving him a vigorous blowjob (‘priming the pump’, we liked to call it); I rubbed my boobs up and down his shaft, and licked his fat balls and slurped the purple head until he was harder than hard. Then I put the big red juicy crown in my mouth, pressed my tongue against the underside of the head, and jerked him off hard and fast until he came in my mouth with a little wail; gobs and gobs and gobs of hot, sticky, salty-sweet boy-come. I swallowed with gusto.

Preliminary business taken care of, we raided the dresser drawer. I packed a nice fat pipe full of pot, and we got stoned.

All high and giggly, I lay down on the bed, and Henry proceeded to eat me out, a skill he had been perfecting over the last few weeks in his parents’ dingy basement.

He was really good at it, too. He knew how to find my clit with the tip of his tongue, and knew exactly how long he could avoid touching me there before I would self-immolate with pent-up frustrated desire. One or two fingers kept slipping in and out of my juicy, slurpy pussy as he licked all around down there, nibbling my thighs to make me jump, and just occasionally lavishing some focused attention on my needy clit. Pretty soon I was squirming all over the hideous pink sheets, literally begging him to suck my clit and let me come.

Instead, he flipped me over on my stomach, spread my ass like a ripe peach, and started licking up and down between my cheeks, dragging his tongue up and down my crack. It was something I’d wanted him to do, but he never had, and I had never asked for it. It was absolutely heavenly! Every time his tongue brushed against my asshole, I jumped and groaned out loud. I was shockingly, unbelievably wet. I was making a massive wet spot on the sheets, and still he kept licking. He concentrated on my anus, and it felt like his tongue was drilling it’s way meters and meters up into my ass. Meanwhile, he was still fingering my pussy. I came two or three times like that, his tongue buried in my asshole, his fingers tormenting my pussy and clit; little, speed-bump orgasms like distant thunder that foretold a massive come looming on my horizon.

“Stop it!” I gasped at him “Stop what you’re doing and fuck my butt hole!”

We didn’t have any lube with us, but we found a bottle of extra-virgin olive oil in the kitchen that we figured would work ok. Henry’s cock was hard all over again, bobbing cutely as he walked. I got on my hands and knees in the center of the bed, and he poured oil all over my backside and slathered his dick in the stuff.

He finger-fucked my butt a little bit, but I was too impatient for that. “Just stick it in!” I whined. I didn’t think I could take much more torture. The anticipation was killing me.

I was a little afraid it would hurt; I’d experimented with my own wet fingers before, but I’d never had anything as large as Henry’s cock actually up inside my butt. I needn’t have worried; he was almost too gentle and careful, and his dick slid right up my asshole like it was built for the purpose.

It was amazing! He seemed hesitant to fuck me really hard and deep, so I started rocking back and forth, impaling myself on his cock, forcing it deeper and deeper up my ass. I felt so full and sensitized and stretched to the limit! My pussy was drooling liberally, my tits were shaking, my clit was bulging out like a mini-erection.

Together, we slid past the point of no return. Henry started fucking my butt hard and fast. It was incredibly intense, right on the borderline of what I could take. We were both making a lot of noise, crying out loud with every thrust. I could feel his balls slapping against my engorged labia, the wetness running down my thighs.

I didn’t even have to touch my clit. I came, came hard, and it was like Hiroshima going off. Spasms rocked my entire body and I jumped and squirmed on his dick, setting him off as well. I could feel his dick pulsating inside me, pumping semen deep into my asshole.

We caught our breath for a few minutes after Henry extracted himself. We kissed and cuddled on the bed, his soft wet cock nestled between my butt cheeks. I could feel his come leaking out of me. Henry got up and used the bathroom and washed himself off.

Vince’s camera was out on the bedside table. I picked it up and turned it on while Henry was peeing. There were a bunch of pictures on it, a recent trip to the zoo with the wife and kid, a visit to the grandparents. Nothing dirty or sexy.

We helped ourselves to a little more of Vince’s pot. Then I fished my dildo out of my backpack (I had developed a nasty little habit of taking it with me everywhere I went), and I had Henry take a bunch of pictures of me masturbating.

I guess that turned him on all over again, because before I was finished, he had to set the camera down and jerk off onto my wide-spread pussy while I frantically fingered my sore, swollen clit and jammed the plastic toy against my tender asshole. He didn’t produce a ton of come this time, but when he did come, dribbling pearly white semen onto my splayed-out pussy, it was just what I needed to set me off one more time, and I came too, bucking and writhing, gasping for breath, my tits flushed red and my clit too tender to be touched.

Then we got all paranoid that someone would come home. We’d lost all track of time. We got dressed in a hurry, and straightened out the bed a little. The sheets were a mess; between my juices and Henry’s come and the olive oil, there were stains all over the place. I put Vince’s camera back where it had been on the table, and we made our exit, locking the door behind us, Henry still technically a virgin. For the time being.

We had a lot of fun together that year, me and Henry. We ended up getting together with another girl from school, Natasha, who I had known for years, but never really gotten to know. She wore all black, all the time, and never wore make-up. She spotted Henry’s panties down the gap in the back of his jeans in math class, and started following us around until we just naturally got together. It turned out she was smart, cynical, funny, deeply perverted, and an amateur cinematographer into the bargain. The three of us got along really well, and had some crazy adventures together, which is a different story entirely.

I’ve never come across the pictures that Vince took of me, though I’ve certainly spent plenty of wasted hours browsing through random homemade porn on the internet. They’re out there though, somewhere. I can almost guarantee that.


Comments (3)