Olive, Female, 31

	- 5'5, 140lbs, pale, slightly-freckled skin, dark-brown hair shoulder-length hair

Olive has a very strange fetish

The first time she suggested it, I was horrified. It wasn't anything gross or extremely dangerous, nothing like that. I'd only known her for two weeks, though, and we'd gone from passionately making love to her dropping in my lap an act which, at first, I refused.

“I want you to fuck my ass while I sleep. Hard. Like, don't hold back or anything. I won't wake up.” she'd told me as we rested on the bed after I'd cum in her mouth. We were not even to the point where we trusted each other enough to stop using condoms for intercourse. I'd not so much as touched her butthole. I'd only known her a few weeks, and we'd been dating for barely two. We weren't really to the point where I thought we should be surprising each other with unusual requests.

Sure, on the surface, you might be someone to jump at the chance to do what she wanted. But, I must admit, to me, it sounded horrible. Why would I want to fuck a sleeping woman? She'd not even be reacting, into it, moaning, encouraging me, fucking me back as hard as I fucked her. All my experiences with women had been awake and with both of us taking part. The way she asked for it made it sound like rape. Even though she gave her consent, the act itself sounded like something I would not want to do.

We nearly broke up over it. I'd asked Olive exactly what she meant and she told me, “I take an Ambien and get really knocked out, like, really out. I don't wake up on that shit. Like, I don't even move. Can't move, I think. So, I'll be all out of it, and then you fuck my ass really hard, like, so hard you think it hurts. When I wake up in the morning, I'll be super sore and know you did it, like, really did it.”

I had stared at her, open-mouthed, unable to understand why anyone would want that. Who wanted to feel helpless like that? Why would I ever want to treat a woman that way? I was seriously second-guessing our relationship. This woman had issues, from my perspective, and though I stayed the night with her after refusing her request, I spent several days avoiding her while I tried to sort out in my head what the fuck was going on.

I asked a couple of buddies, guys I knew who had more experience than me, and they acted it like it was the best offer they'd ever heard. Why wouldn't I go for it? She wanted it, they told me. So give it to her, they said. She's crazy, sure, but hang onto any woman that far out-there in bed. When asked whether they'd ever known a woman wanting such a thing, both admitted they had not, though one said he'd had a partner for a couple of years who was very submissive and loved to be fully restrained, ball gag and all, and he figured it wasn't really much different.

When I'd pointed out that at least his partner had been awake and could have signaled for him to stop, he shrugged and suggested I was overthinking things. I was not certain that was so.

I didn't break it off with Olive, though. I really did like her. She was smart and fun to be with. We shared a lot of the same interests and values, at least outside of unconscious sex. And I cared about her, too. Her brother had died a few months earlier when he was only thirty-four. She was three years younger and had had a hard time picking up her life. That's how we met. She'd started playing racquetball at the same club I attend, and we'd been matched up to play one afternoon. Just a random meeting which led us to start dating.

I tried to rationalize what she wanted. Had she been raped? Abused by her father or brother, maybe? Was she manic? Deeply depressed? Did she hate herself? I knew those things could easily hide under carefully-displayed masks, so it sure was possible.

But after a few days, I called her and we met at her place to talk. I laid out my concerns. I told her that I really liked her and I thought we were good together, in bed and elsewhere, and I didn't want to stop seeing her. I was really rattled by what she wanted to do, and I needed some answers about why it was her desire.

Olive was quiet a moment and then explained. She'd had a boyfriend a few years earlier who introduced her to bondage play. At first, it was just light stuff, but it grew into a full Daddy Dom / Little Girl sort of relationship which featured a strong angle of power and dominance. She mostly enjoyed it, though he was too intense at times and didn't always listen to what she wanted.

He'd been the first one to try fucking her while she slept. She woke one night to feel pressure in her ass, then realized the guy had pushed his dick inside her in the dark and was slowly sodomizing her. It didn't feel terrible, and she didn't make him stop. Instead, she actually rather enjoyed it.

This grew into times when she'd pass out drunk and he'd fuck her pussy and ass. Sometimes, she woke up in the middle of it, groggy and uncertain what was going on, but what she began to fantasize about was the feeling she had when she woke up. Olive remembered a morning after she'd gone to bed with a headache and taken strong painkillers. Her ass was sore as she blinked awake. Really sore. She felt like she had diarrhea and rushed to the bathroom, only to push out a small, squishy stream. She put together what had happened and realized her boyfriend had cum in her ass while she was completely out of it.

Olive didn't know why it had turned her on, but she told me it was the strongest orgasm she'd ever had, masturbating on the toilet, that guy's cum dripping out of her sore, raw asshole. She told the guy she wanted him to do it again the next night, and he scored some really strong pills which would make sure she didn't wake. When she woke up again, her ass very sore, she knew she was hooked. They eventually broke up when the guy got arrested for insurance fraud, but she still longed for a partner willing to let her have her fetish.

I let all of that sink in. I mean, really, what guy wants to hear about some intense, rough sex the girl he was dating had with some other guy? That was a bit of a gut punch. But I got past that quickly. She was with me instead of him. I admit, learning that she wanted to be fucked in her ass while she slept because she liked it, not because she'd been abused, was the key for me. We talked more over the following days, and I agreed to give it a try. I was still unsure that I would enjoy fucking an unconscious woman, but I figured I'd try anything once.

So we went out to eat on a Friday night. Olive looked beautiful. Her round, moderate frame held a few extra pounds, sure, but she wore it well. The tight, black slacks she wore without underwear made her ass look delicious, and her round breasts were accented by the plunging neckline of her sheer, green blouse. Olive wore her hair up in a loose ponytail, the dark-brown strands slick and shiny, contrasting nicely with her pale, lightly-freckled skin. She was clearly excited for what would come later, and I admit, I was both aroused and nervous, myself.

After we returned to her place, we stepped into her bedroom and sat on the edge of the bed kissing. Olive had already taken an Ambien and she said it would only be a few minutes before she fell asleep.

“Listen, you can go easy tonight,” she told me after pulling back from a kiss. “I know I weirded you out with all this, like, I'm sorry. Just remember that I want this, and it really turns me on thinking this is really going to happen. My pussy is wet.” Olive took my hand and pressed it against her crotch. The thin fabric of her slacks was damp and warm.

“I promise I'll try,” I told her. “So... I guess we just wait?”

Olive nodded. “I love trying to fall asleep while making out.” She stated it smoothly as she pressed her lips to mine. I caressed her sweaty genitals through her slacks.

Within moments I could tell she was getting tired. Her body was relaxing, sagging. I suggested we take her pants off first, but she just smiled and said it would be more fun to wait. We kissed more when she stretched out on the bed, fully clothed, on her stomach. I ran my hands over her ass, so horny I could hardly keep from jerking off.

Olive blinked twice, then smiled wearily. “See you in the morning...”

I watched as she fell asleep, almost in mid-sentence. Her breathing became smooth and deep, her mouth slightly agape.

I froze in place, beside her, for a long time. I admit it felt weird with only my hand on her ass. I struggled with the big part of me which screamed this was a violation.

But I knew she wanted it. Expected it. Perhaps needed it.

I grew bolder, smacking her ass lightly a couple of times, then grabbing hold of a buttock and squeezing strongly. Olive didn't stir, and only barely seemed to register the contact. I slid a hand down the crack of her ass and felt the moist warmth between her thighs. The slacks were pulled tight against her crotch and I could make out the matted bristles of her pubic hairs through the fabric. I caressed her vulva a moment, then lightly smacked Olive's crotch. She still didn't move.

My cock was full erect and straining for release. I undressed quickly and stood stroking myself while I looked at Olive on the bed. Her round, full ass was prominent and so arousing. I wondered briefly how to get her slacks off her body.

It was in that moment I realized I'd actually moved past my inner questions about whether I could do what she wanted, and instead I was eagerly planning how to get started doing so.

I closed Olive's legs as tight as I could and then straddled her thighs. Reaching under her abdomen, with effort I found the button on the front of her slacks. A few fumbled motions later, I pushed it through the hole and was able to slide the zipper down most of the way. I grabbed hold of the waist line and pulled.

It moved a few inches over her ass, but hung under her stomach. I reached an arm under her body and used that leverage to drag the slacks down past her ass and over her thighs. I was so turned on by what I saw, what I was doing, that I didn't bother yanking them all the way off. I pressed my face against Olive's crotch and lapped against her anus and her pussy. I tasted brine and arousal, bittersweet hints on her butthole, and rich, pungent discharge from her vagina. I lost myself a moment in licking my girlfriend's delicious holes.

All this time, there'd been little more than faint noises from Olive, a bare recognition that I was freely violating her body, touching her private parts while she slept. Even when I reached a hand into her crotch and rubbed her clit, she only sighed very lightly and her hips shifted slightly just once. And then she was still and silent, her breathing smooth and moderate.

I couldn't wait any longer. Whatever she was experiencing, I needed release.

I moved myself until my thighs were straddling Olive's hips. Leaning over her back, I held my body up with one hand while using the other to guide my cock to her anus. I felt the spongy, tight hole press against the head of my dick. It was wet from my rimming and ready for my penetration. I'd never fucked Olive in the ass before, and this was an extremely unique way to finally do so.

Tight, tense heat wrapped around my penis as I slid inside Olive's butt. I paused only briefly, halfway inside, to see if she was reacting. Her hand had moved from near her face to her side, but otherwise, she showed no signs of the hard dick throbbing in her ass.

I let go my reservations, fully committed, and pushed myself deep into Olive's bowels. My groin pushed against her soft, full buttocks and I rested over her, enjoying the pulsing heat inside her body. Her guts felt squishy and hot, silky and pliant, still tight enough to wrap firmly around my length. I knew I was drooling precum freely into Olive's ass.

I pulled back smoothly then thrust inside. My body vibrated with excitement and arousal. Olive's anus gripped in a tight ring as my penis moved in and out, and before long, I could smell the results of my sodomy.

At first it was strange to have no deliberate resistance. Usually, the woman would be fucking me, too. Moving her hips in some way, grunting, moaning, her fingers grasping at the sheets or rushing down to her tits or clit or pawing over my chest or butt.

Olive's body gave only passive resistance, the soft and firm cushions of her ass cheeks and the spongy ring of her anus absorbing my thrusts. She made almost no noise beyond a forced, random exhalation of breath.

She was completely unconscious as far as I could tell.

I became stronger, more powerful. Olive was still and quiet below me. I let my weight fall over her more fully, pressing down her body. She squirmed lightly but then stilled again. I could hear her breathing faster than before.

I moved my hips up and down, her backdoor becoming slippery and opening more fully to my penetration. My cock burned from within, radiant shards of pleasure rushing into my body. My mouth dropped open and I started to moan loudly. The tip of my dick was on fire by the time semen exploded from my small hole and into Olive's receptive bowels.

I held firmly against Olive's body, twitching as I emptied myself into her ass. It was a big load, pressurized, and my ejaculate fired out over and over to fill Olive's guts with my seed.

I felt overpowered a moment. I'd liked it too much. She was mine to use. Her body fully mine. She didn't resist. Couldn't. I could do what I wanted to do. It worried me even as the last of my cum drained out of me and into her ass.

I held still, my weight resting on Olive's body. I readied to withdraw, to figure out how I felt about what I'd just done.

And then she sighed.

It was pleasant. I heard a smile in it. “...mmmm...mm...”

Whatever it was, my dick responded by jerking a couple of times. The heat of Olive's butt radiated through me and I stayed hard. I was soon fucking her ass again, her anus slippery and a bit sticky. I didn't slow down. No, I fucked her harder, harder. I wanted to give her what she desired.

I began to really like what I was doing to her. Olive had said it would give her pleasure. Turns out, it gave me the same. It was an amazing thrill to fuck her unconcious body, and I lost myself in the power and control and strength I felt in those moments.

I knew she was becoming raw. I could feel it. My cock burned along my shaft. Her anus was dialated, gaping, much looser than it had been.

Olive said she wanted to be sore in the morning. I pounded her for a good thirty minutes to ensure I'd done my best, and by the time I spewed my second load into Olive's guts, I had no doubt she was going to feel it when she woke up.

- - -

The next morning, I felt Olive stir. I'd slept only lightly. While my mind had been surprisingly free of second-guessing, or much of anything but how much I'd enjoyed what we'd done, I'd been unable to quiet it enough to do more than doze off and on.

I opened my eyes to see that Olive was in the same position she'd been in when I'd pulled my lightly-soiled, slippery penis from her abused butthole. Her ass was still exposed as she lay on her stomach.

I saw her eyes flicker without recognition, then they closed again for a few minutes. She woke again, and this time her eyes watched mine a moment before she said sleepily, “...good morning...”

“Morning,” I replied, leaning towards her to kiss her lips.

Olive smiled, her eyes closed a moment, “Mmm... Mmm... my ass is sore...”

“I bet...”

“So sore...” She was practically purring. With effort, I saw her move her hand under her body and into her crotch. I realized she was masturbating. “Hurts so good, like... mmm... so good...”

Her hips began to rise and fall as she played with herself. She was still groggy, so it was almost half-hearted, but she kept at it while I watched. I grew erect quickly.

I knew something she'd like even better, or so I hoped.

Before she could cum, I moved over her and pushed my cock against her anus. It was still slippery and sticky, the ripe odors of our anal sex thick on her body. She groaned as I plunged into her ass quickly, then cried out as I started to fuck her. I knew it was uncomfortable. Probably painful. But within a few seconds of my sodomy, Olive started to orgasm below me.

I slammed in and out of her hole while she came, her cries louder than I had ever heard from her, much more vocal than the reserved way she usually came. I heard her mix of pain and euphoria, and I kept fucking her hard.

Olive kept masturbating, and in moments she came again, then a third time soon after. It was only when I couldn't hold off any longer that she finally stilled. I emptied a small load from an intense orgasm, then rolled off her body, out of breath.

“That,” Olive said, smiling and looking sated, “was a good twist.”

“Thought you might like that.”

I heard a wet sputtering and realized the air trapped in her rectum was escaping through slickness and globs of my sperm.

“Sorry... very relaxed right now,” she said without shame.

“Nothing to be sorry about,” I replied, “compliments to the chef, or something like that.”

Olive laughed, then let out a contented sigh. “Might be hard to sit this morning, but believe me, I'm not complaining. That... was perfect.”

We kissed a while and relaxed on the bed. She asked me, “so... you think you might want to do that again some time?”

“I can't wait...” I said honestly, “and... I think we should talk more about you being tied up...”

Olive purred her approval, “I knew you were going to be fun...”