This story is entirely fictional and the product of my imagination. All characters are over the age of 18 years-old. CW: drug use
Olivia (that was the name she used, though she later did tell me her real name) was a prostitute I encountered on an unnamed website, back when that was a thing, and we met several times over the course of a year. We always had a good time. Or at least I always did, and she was enough of a professional to make it seem that she did as well.
Olivia was tall for a woman, maybe five-nine or five-ten. She was thin, not skinny though. Her hips were nicely rounded and had an ass shaped like an inverted heart. Her breasts were small and firm; either a large A cup or small B cups. Olivia's dark blonde hair hung to just below her shoulder blades when she wore her hair down, though it was usually piled up on her head in a messy bun. With her light brown eyes and pale skin, while she was not model beautiful, I found her long neck and shapely legs very attractive. Her personality was very accommodating, usually, but she did have two absolute rules: no vaginal sex without a condom, and absolutely nothing happening with her ass; no fingers, tongues, nothing at all.
In July of 2018 I was finally living alone, so rather that going to Olivia's in-call I asked her to come by my place for an hour or so. She agreed and told me the address where Ii could pick her up. That night, rather than staying for just an hour, Olivia wound-up spending the whole night asleep in my bed. In the morning, I left her there sleeping deeply; it seemed like she could use the rest. I went to the gym for my daily two-hour session and when I got home I found Olivia still in my bed, propped-up against some pillows, passed out with a hypodermic needle in her hand. Olivia was an intravenous heroin user. That explained her long sessions in the bathroom with the sink faucet running. Honestly, this revelation did not come as a huge surprise and shock to me; I had suspected something like this and it really didn't bother me much.
Long story short, the next week Olivia was back in my bed. We talked a bit about this and that and she told me that she had gotten ahold of some really strong stuff, much stronger than her usual tar heroin. She suggested a little game: we could have or usual session, but after she would shoot-up and let me do "whatever I wanted" while she was nodded out. I eagerly agreed to her proposal and confessed that I had a kink for nonconsensual role-play. It's a kink that I've never been really comfortable indulging in with prostitutes, only with long term girlfriends so it had been couple of years. I promised Olivia that I wouldn't do anything that we didn't agree to before-hand, but I had one request: that she needed to act as if she didn't want it to happen; struggle and protest while I did it anyway. Her two requests where that I not hurt her—no slapping, biting, punching or spanking—and no anal play. Everything else was fair game.
Olivia had our usual session—or a variation on it. She liked it when I held her legs back hard when we fucked in missionary so I could thrust my cock into her deep, fast, and hard. But she really liked it when I flipped her over onto her front and fucked her doggie style. Something about this position made her cum really hard and the pulsing tightness of her pussy in this position usually meant that my orgasm wasn't far behind hers.
Afterwards we got ourselves cleaned up and Olivia got out her kit, made her shot, injected it into a vein in her arm and promptly began to nod out naked in my bed next to me. I watched as she did this. I then capped her syringe, took off the sock that was wrapped around her arm and watched her. She lay on her back, breathing slowly, and her rhythmic breathing and my earlier physical exertions conspired to lull me to sleep.
I woke up about 2 AM and Olivia hadn't moved off of her back, but she had kicked off the sheet that had covered her. She looked so quiet and peaceful laying there so I sat up to admire her body in the light of my bedside lamp. Then my inner pervert had a marvelous idea. Carefully scooting closer to her, I gently took Olivia's right hand and wrapped it around my growing erection. I didn't want to chance waking her up, not yet at least. I used her hand to stroke my cock and bring me to full hardness. All seven inches standing full and proud with Olivia's hand wrapped loosely around the base. I would have preferred to use Olivia's mouth, she liked sucking cock—as long as I was careful to not jazz in her mouth, but I didn't trust her to not reflexively bite my penis in her sleeping state.
