Cast:

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.