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One Eye Open

Category: Anal Sex
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My girlfriend’s roommate did it to tease me.

She did it almost every morning, right in front of me. I tried not to watch, but it was impossible. And every time she did it, I went a little more crazy.

And finally, one day, I couldn’t take it any more.


I was asleep, in that hazy, gray-black state just before true consciousness sets in.

I flipped a few switches in my brain and turned on my senses. I was lying on my side. I was in a bed. Not my bed – the pillows were too soft and fragrant. Behind me was a cold, flat surface, probably a wall. In front of me was a heat source, certainly a body. I was spooned against it, and judging by the soft curves pressing into me, it was female. Our bodies fit almost perfectly together. Her back was against my chest, her rump nestled against me, our legs intertwined.

I inhaled, breathing in the sweet honey smell of a woman’s hair. Then I turned on my ears and listened. Her breathing was slow and even. She was asleep.

My ears picked up other sounds. I heard the robins outside, chirping away, getting their early worms. Soon there would be the sound of footsteps and young voices, as the dorm came to life and students groggily made their way to their morning classes.

Thankfully, my first class wasn’t for hours. But my girlfriend, Jill, would be rising soon to make Western History. I looked forward to feeling her body stir. Sometimes we made love before she went to class. It was usually cold in her dorm room in the morning, and she would joke that sex was the next best thing to a heater.

But before she woke, something else would happen. Something that happened almost every morning. Something that hacked away at my sanity, chip by chip, day by day. I knew if I opened my eyes, it would start. Maybe today I could keep them closed, I thought. But then I’d miss it, and part of me wanted to see. I might wrestle with it for a while, but inevitably I’d give in. So, like any good lemming running headlong toward the edge of a cliff, I opened my eyes.

The dorm room was small. The walls were cinder-block, painted year after year with so many layers of white paint that the grooves were starting to disappear. There was a sink and a mirror between two large wall-mounted closets. Next to them, two wall-mounted desks. And apart from them, two beds.

In one bed, I lay, my back against the wall, facing the room. Jill lay in front of me, spooned against me, our bodies buried under the thick covers. In the other bed lay Vicki, Jill’s roommate. And she was staring right at me.

Our eyes connected. Her gaze was bright and clear. I wondered when she woke up in the morning. It seemed she was always conscious before me. Waiting. Watching. Listening, no doubt, for the tell-tale signs of my breath becoming uneven, signaling my march into consciousness. If that was the case, did she know how long I lay there some mornings, debating whether to open my eyes? I wondered.

Vicki’s eyes were dark bluish-violet. Her hair was deep red. She had pale skin that freckled, so she wore sunscreen every day. As a result her skin was like porcelain, almost as white as the down comforter that was wrapped around her like a cocoon. I could only see her face peeking out from the mass of blankets, blinking at me calmly like a snow-owl. She looked almost innocent this morning, like an Eskimo papoose in it’s ivory swaddling. Perhaps I could ignore her, and just go back to sleep.

Then her lips curved up in a wicked smile, and I was caught.

There was movement under her comforter. The cocoon split open. The mass of blankets parted, and in the crack I could see Vicki’s white belly. Despite the cold of the dorms, Vicki slept in the buff, which accounted for her mammoth pile of blankets and comforters. Vicki widened the gap in her blanket-igloo, and I saw her hips, her bare thighs, and the little triangle of reddish hair between her legs.

Vicki slid her pale little hand down her belly, past her belly button, and into the tangle of hair. Her fingers slipped easily between her lips. She was wet. I wondered, did she get off like this every morning, or just when I was around to torture?

I could feel Vicki’s eyes on me. Making sure she had caught my attention, she rolled over inside her cocoon. Her face disappeared into the blankets, as did her thighs. I watched the gap in the blankets expectantly. Then, to my guilty delight, her pale ass presented itself to me.

Vicki had a spectacular rump. The skin was pale and pure, stretched tight over the firm, round glutes. Then the cool morning air hit her skin, giving her goose-bumps, and sending a shiver up her spine. Vicki wiggled her ass, getting comfortable.

And so my morning torture session began. Torture, because of one unfortunate fact. That unfortunate fact was a number: 736. It was the number of days I had gone without having anal sex with a woman.

I felt Jill’s body stir in her sleep next to me, as though my very thoughts were giving her nightmares. 736 days also happened to be approximately the amount of time Jill and I had been seeing each other. But that was okay – we were crazy in love, and sacrifices have to be made. And usually when you go without something for long enough, you can forget you ever wanted it in the first place.

Unless, of course, someone reminds you. And continues to remind you, every morning when you wake up.

In front of me, across the room in the other bed, Vicki wiggled her reminder at me. Vicki had moved into Jill’s dorm at the start of the semester, and apparently heard Jill and I pillow-talking late at night. Shortly after, my morning torture sessions had begun.

Now, it was almost routine, and yet anything but mundane. As Vicki’s delicate hands slid into view, and she placed them on her hindquarters. She caressed her lucious curves, warming them up against the cool morning air, and I felt hot arousal pumping into my blood. I watched intently as one of her hands disappeared under the covers. It came back with a crystal-clear dollop of K-Y jelly on it. She spread her cheeks with one hand and slipped the lube between them with the other.

Vicki probed her anus with her slick index finger, rubbing the small muscle into relaxation. Then she started to stroke in and out, slowly, her ass moving slightly to meet the penetrating digit. As usual, her free hand went around front to massage her clit. She slipped a second finger into her ass and began stroking in and out. My erection was growing, and I watched, frustrated, but entranced as always.

Then something changed. Vicki withdrew her fingers from her ass, and they disappeared into the covers. Moments later they returned, holding a long, flesh-colored object, in the shape of a cock.

My erection sprang to fierce attention as I realized what I was about to watch. Vicki didn’t hesitate. She spread some of the clear, goopy lubricant across the stick and pressed the head between the soft cheeks of her ass. She worked it in slowly, and inch by inch the length disappeared into her. Then her free hand went back to her clit, and she started stroking the dildo in and out of her ass.

My pelvis moved of its own accord, in time with her motions. Jill’s ass was pressed up against me, and I had the sudden crazy urge to pull my briefs down and ravage her in her sleep. I of course didn’t, but still, I wanted to feel her against me. I quietly slipped my underwear down, freeing my cock. Then I spooned against her again, nestling my length between her cheeks.

Vicki’s bed was squeaking. The pile of blankets was rocking. The dildo slid easily in and out of her ass, her hand making wet little slapping noises against her rump as she fucked herself with it. It gave me pleasure to watch, and I loved the simultaneous feeling of my cock, rubbing up and down against Jill’s butt, the soft, warm flesh massaging me. But I worried Jill would wake up, so I kept it under control.

Vicki came. Her moan was muffled by the comforter and blankets. Her ass tightened, curvy muscles flexing as the orgasm rippled through her, and she drove the rubber cock deep inside her bottom, gasping with pleasure. It was delicious to watch. I squirmed against Jill, wishing my own cock was buried as deep as the one in front of my eyes.

Jill sighed in her sleep, and I felt her body waking up. Vicki heard it too. Her body disappeared into the depths of her covers and the cocoon sealed up. I wondered if I should pull my underwear up.

“Mmm…morning.” Jill said sleepily. She pressed her body into mine, nuzzling against me. Then she stiffened. I felt her hand slide between us. It touched my raging erection.

Jill rolled over to look at me, and I half-lidded my eyes, feigning sleep. She looked at me for a moment, her hand still on my cock. I realized my ‘morning wood’ was a usual occurrence – it just wasn’t usually outside my underwear.

“You awake?” She said. I made some sleepy noises and looked at her. Jill was incredibly hot, even before a shower, makeup or coffee. Her hazel eyes were two deep wells, gleaming out between strands of her long golden hair. Her skin was fair, and smooth, and young. She looked back at me over her curvy shoulder, and I leaned forward to kiss it.

“What were you dreaming about, huh?” She asked knowingly, giving my cock a playful tug. I licked a line up her long, elegant neck to her ear. She giggled.

“Oh, I don’t know.” I whispered, remembering to pretend Vicki was asleep. Jill glanced over at Vicki, or rather at Vicki’s hibernation heap, and lowered her voice as well.

“I think you do know.” Jill accused me. She pressed her ass into my exposed cock, and her eyes squinted, her nose crinkling up. “I think you were dreaming about my ass.” She said.

“What if I was? Can’t a guy dream?” I said. Jill nodded, then leaned in and gave me a big, deep, warm kiss.

“You bet. Do it in your dreams, all you like.” She said, winking at me. She knew it was torture, but I smiled obediently and pulled my underwear up. And I meant to leave it at that, but I ended up opening my mouth anyway.

“Maybe you should try doing it in your dreams.” I said. “You might like it.” Jill groaned.

“Oh baby, you know how I feel about it.” She said, her voice soft but firm. And I did know. I knew the back-story by heart. But I didn’t like it.

“I just can’t believe you’re going to let one bad experience wreck it for you. Aren’t you even curious to try it again?” I pleaded. I felt like a broken record.

And that was Jill’s cue – she rolled me onto my back and straddled me. Her eyes stared down into mine seductively.

“I think I know something that might take your mind off it.” Jill said. She started to slide down my body, her eyes locked with mine, her lips kissing a little trail down my chest and belly. As much as I loved Jill’s fellatio, I knew she’d be late for class.

“You better get to class.” I said, pulling her back up. “I’ll take a rain check.” I said it as appreciatively as I could. Jill looked at me.

“Now you’re going to pout.” She said. I shook my head.

“No I’m not. See? I’m going to go back to sleep, so I can dream. Just like you said.” I closed my eyes and dug into the covers. Jill just sat there, watching me, and I peeked out at her.

“You’re not going to pout?” She asked. “Promise?”

“I promise.” I said. Jill smiled and gave me another drink from her sweet lips. Then she slid out of bed and put on her robe.


I must have dozed off while Jill was getting ready for class. The thump of the door closing woke me up. Startled, I sat up and looked around. Jill was gone. I fell back into bed, ready to slip back into my hazy half-asleep fantasies of you-know-what.

There was a rustle. Something stirred. I opened my eyes.

Across from me, Vicki lay in her bed. It was warmer in the room now, and she had cast some of her coverings off. Now her toes and parts of her legs were visible, the creamy skin melding with the white of the sheets. She lay on her stomach, and her head was turned away from me, her upper body still wrapped in a blanket. But in the middle of the tangle, her bare ass stuck out of the covers, like a mountain peak rising up amid the clouds.

I listened. Her breathing appeared even. Was she asleep? I wondered.

I carefully got out of bed and padded over to the sink, pretending to ignore her. Then, in the mirror, I took another look. Sure enough, she was splayed out on the bed, fast asleep. Her legs were drawn up on either side of her, making her rump stick out.

I turned around. I stepped towards it. I really didn’t intend on doing anything. I just wanted to look. As I got closer, the sun came out from behind a cloud and light streamed through the window. Her pale cheeks glowed in the warm light, and I could see where the jelly had dried on her skin. Ah, lovely K-Y Jelly. I knew if a little water was applied the lubrication would spring to slippery life again, but I resisted the urge to wet my hand and touch her flesh. Instead, I reached into my underwear and stroked myself lightly, remembering what it was like to give a woman anal pleasure.

“Come on, you know you want to.” Vicki’s voice said.

I froze, my hand on my cock. My eyes slowly worked their way up to where her gaze waited for me. Her violet eyes regarded me, up and down, and she smiled. “So go ahead already. I won’t tell.”

And I knew she probably wouldn’t. Jill would never know. She’d never have any idea that after she left for class, I slipped my cock into her room-mate’s ass and got my anal fix. In response to my thoughts, Vicki opened the drawer in her bedside table. Amid the condoms and sex toys lay the tube of K-Y. She pulled it out and squirted a healthy amount on her hand. I watched as she brought the lube to her ass and slowly smeared it across her tight opening. She slipped a finger inside, massaging the muscle a little. Then she pulled her hand away.

“Okay. I’m ready for you.” Vicki said, smiling her wicked-sweet smile.

The war was on, between the head on my shoulders and the head I held in my hand. Vicki arched her back, moving her ass towards me. She looked at me over her shoulder, her violet eyes alternately demanding and begging me to enter her.

But I couldn’t do it. Jill was my baby, simple as that. I sighed, long and deep, and Vicki knew what it meant.

“Oh brother.” She said. “You know she’s never going to give it up.” Vicki accused. I shrugged, and pulled up my underwear. To make it feel even more final, I pulled on a pair of pants. I fastened the belt like I was locking a door.

Then I walked over to Jill’s bed and slumped into it; I suddenly felt very tired, and I just wanted to sleep, and perhaps to dream. The covers smelled like Jill, and it felt good to know I could greet her with a clear conscience when she came back from class.

“You know, I could tell her you’ve been watching me all these mornings.” Vicki’s voice prickled across the room at me like static electricity. My stomach tightened. I rolled over to look at her.

“You wouldn’t.” I said. Vicki smiled at me wickedly. Of course she would.

“I could be persuaded not to.” She said. “But you’re going to have to do me a favor.” Vicki gave me puppy-dog eyes and wagged her ass slowly in the air, back and forth. I couldn’t believe her persistence. I realized she wasn’t just trying to do me a favor. She wanted it, bad.

“Sorry.” I said, trying to stifle what was left of my erection. “Maybe you better go ahead and tell her. I feel guilty as it is.”

Vicki rolled her eyes at me, letting out an exasperated breath.

“You’re incredible.” She said. “After all these mornings, putting on shows for you, I thought you’d be easy prey.”

“Sorry.” I said. I knew I should elaborate, but instead I pulled the covers over me and closed my eyes. I wanted to escape into unconsciousness.

And escape I did. But as I drifted off to sleep, I faintly heard a sound.

It was the scratching of a pen on paper.


The door closed with a quiet thud.

My brain stirred to life. The sensors came on. I was in bed. Jill’s bed. I was on my back, splayed out in a spread-eagle, which meant I was alone on the double mattress.

Jill’s voice hummed quietly in the dorm room. It gave me a warm feeling in my belly. Then I remembered my encounter with Vicki in the morning, and the feeling turned cold. As if reading my thoughts, Jill’s ceased humming. I peeked my open to see the reason.

Over the sink, there was a piece of paper taped to Jill’s side of the mirror, with her name written in feminine cursive on the outside. Vicky had written Jill a note! My insides went all topsy-turvy with fear and guilt. I didn’t know what to do, so I just pretended to sleep, keeping one eye half-cracked to watch Jill’s reaction.

Unfortunately she turned away from me as she read the note. I stared at her back. Would she turn around crying? Or yelling? Would she throw something?

Jill turned. Her face was thoughtful. She folded the note up and put it in her pocket. Then she walked towards me. Worried she could see my open eye, I closed it. Her footsteps neared and stopped. I struggled to keep my breath even.

Then I heard a noise – a dragging noise. She was opening a drawer. What was she looking for? Objects flashed through my mind: scissors, a hammer, a plastic bag, a can opener. God, please don’t let her try to kill me with a can opener…

Her footsteps neared again. Then a pause. I felt something drop onto the bed next to me. I could only imagine what it was. Probably scissors, I thought. Then I felt something terrifying – a tug at my belt.

I cracked my eye open. Jill was carefully, quietly, gently undoing my belt.

I panicked. I had heard this greusome urban legend, and I knew how it ended. Now was the time to jump up and run. But I looked at her face, and her expression was odd. She was smiling a little, and she had a nervous excitement in her eyes. She certainly didn’t look like she was about to castrate me. I waited and watched.

Jill got my belt undone, and peeked up to see if I was awake. My ruse held, and she carefully tugged my pants down so as not to wake me. My underwear came next. My penis was limp. Jill reached down and touched it gently. She carefully stroked the flesh with her fingernails, trying to coax me into an erection.

So that was her game. She was going to get me hard and then…what? I risked blowing my cover, and peered down at what lay on the bed next to me.

It was Vicki’s tube of K-Y jelly.

Whoah. What was going on? What had Vicki written in that note? My gears turned.

Meanwhile, blood rushed into my cock, making it swell in Jill’s hands. I tried not to betray my excitement. Jill peeked at me one more time before reaching down to undo her own belt. Her jeans slipped off and she stepped out of them. Her fingers tugged at her underwear, pulling them over her firm ass and down her legs.

Then she carefully inched onto the bed. She put her weight on one knee, then the other. She winced as the bed creaked, her eyes darting up to mine. I was barely able to see out of the tiny slits of my eyelids, but I watched Jill get into a crouched position, facing away from me.

Now that her eyes were off me, I could open mine. Jill still wore her sweater, but below it her bare waist widened out into her lovely hips. Below those hips hung the perfect curves of her ass, firm and round.

Jill reached down and took my cock in her hand. She reached for the tube of K-Y jelly and popped the cap. Like spreading toothpaste on a brush, she squirted out a long line of gel along the top of my cock. Her hand carefully spread it across the length, until the whole muscle was coated in a clear sheen. Then she put a little more jelly in her hand and reached back behind her.

It was cute to watch her search for her own opening, the tight little muscle nestled between her cheeks. She found it and daintily patted some lube onto it. I wanted to reach up and help her, but I clenched my hands, remembering that I was supposed to be asleep.

Jill set the tube of jelly down and took a deep, nervous breath.

She aimed my cock upwards, and scooched her knees back a little to line herself up. I watched as Jill’s ass dipped down, searching for me. The tip of my cock kissed her anus lightly, and she held it there. Her hand was shaking slightly.

Gaining resolve, Jill began to push her ass down on my cock. It wouldn’t go in at first; she was too tense. Again, I wanted to help, to use my fingers to massage her into readiness, but I knew I might wreck the moment, so I let her go.

Jill tried again, this time forcing calm, deep breaths as she probed with the head of my cock. The tip slipped into her, just a little, and she stopped, holding it there, feeling it inside her. Then she lowered her body a little more, and the head disappeared completely inside her ass.

I was in heaven. I willed myself not to come right then and there. Jill cautiously continued, moving her ass down incrementally, taking in a half inch at a time. Once it was halfway in, she held still, then backed out a little, feeling it massage her channel. It must have felt good, because a tiny moan escaped her lips as she slid her ass up and down in my lap.

Jill was ready for more. She took another inch inside and gasped. Her fingers felt my cock, measuring how much was left to go. She decided she could handle it and pressed her ass down until my cock disappeared inside her completely.

Jill was straddling me, her legs on either side of mine, her soft rump resting on my pelvis. It felt incredible to be up inside her, deep inside the territory she had forbidden me for so long.

Jill put her hands on the bed in front of her and used the leverage to start moving her ass up and down in my lap. She started gently at first, still cautious of the new sensations, but soon her body was rocking back and forth. My cock stroked in and out of her ass easily now as her muscles relaxed and the lube worked itself up inside her.

One of her hands left the bed and went to her pussy, and though I couldn’t see I knew she was giving her clit some attention. I prayed she would come soon, because I was desperately close.

“Oh fuck.” Jill hissed, and I felt her anus dilating on my cock as her orgasm ripped through her. She rode me harder as she climaxed, and I lost control of my organ. It throbbed with electricity, my balls tightened, and the first jet of hot semen pumped up inside her.

“Unh…I can feel it…” Jill moaned, her ass slowing as she felt the new sensation of my cum squirting up inside her. Her anus continued to flex, milking it right out of me, until I was utterly spent. Jill stopped moving and her ass pressed against me. We sat like that for a few long moments.

Then Jill leaned her weight forward. She slowly raised her ass up. My cock, still partially erect, slid slowly out of her. Once it dropped out, Jill got up on wobbly legs and shivered. Then she turned to look at me.

There was no sense in pretending to be asleep now, so I looked back. She had a satisfied, exhausted look on her face.

Jill crawled up the bed to me and pressed her body against mine. I wrapped us up in the blankets, and we nuzzled together, getting warm. She looked up into my eyes.

“So…have a nice sleep?” She asked.

“Mm-hmm. Good dreams.” I said.

”Yeah.” Jill said, giving a shudder. “Me too.” I laughed. I wanted to say something to the effect of ‘I told you so’ but I kept it to myself.

“What did Vicky’s note say?” I asked. Jill looked up at me.

“It said she was sick of listening to us argue, and that I didn’t know what I was missing.” Jill said, her face turning red. “And then she told me where she kept her tube of jelly.”

I laughed again, and Jill laughed with me.

We fell asleep, our spent bodies entangled under the covers.


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