I was kind of a loser in my early 20's. I was a virgin and had no prospects whatsoever. It's not like I was ugly, I was just shy and awkward. Then I got a job waiting tables at an upscale restaurant and met Shelly.

Shelly was the 18 year old daughter of the owner of the restaurant I was working at. She had jet black hair, sky blue eyes and bubble butt on her narrow frame. I figured I had no shot since I was black and her family was rumored to be kinda racist. I guess she wanted to rebel because she gravitated right for me.

She had to initiate everything because I was so awkward, but she didn't seem to mind. She asked for my number. She started texting me, then calling me. She asked me out for our first date, but I still paid. Then she asked if she could kiss me when it was over. The kiss was chaste and sweet, but it something unlocked in me and when she tried to pull away I stopped her and held her close. Her body melted into mine and what started as an innocent kiss turned into a ridiculous, passion-filled young people makeout session. It was slobbery and sloppy and immature and lusty and crazy and the greatest thing that had ever happened to me.

On our second date she gave me head for the first time. She was horrible at it, all teeth and jerky movements, but i didn't care because her face was in my crotch and I was horny as fuck. I'd seen enough porn to think maybe I could try some freaky shit so I started pushing down on the back of her head to force her face down on my dick. She didn't resist, but after a couple minutes she came up for air and looked at me funny. But when she went back down on me she started gagging herself and moaning. A few minutes later I came so hard i almost passed out.

After a couple months of secretly dating and fucking we had all kinds of sex adventures fucking in my car, her bedroom when her parents were away, all over my apartment, and whenever we could in the restaurant as well. She even had the special keys to the offices so she could ride me in her father's leather-bound ergonomically-designed office chair. I must have dumped gallons of semen into her pussy which was stupid, I know, but I trusted her when she said she was on the pill and was so fucked up with my first regular ass that I wasn't thinking straight.

Three months into the relationship we were at my place and she said she wanted to try some really kinky shit. We'd watched some porn together and she wanted to try having me tie her up and fucking her however I wanted. Those were her words. I figured everything was on the table. Hindsight. 20/20.

She picked her safeword ('yellowstone' because she loved hiking there)and we started to do our thing. I tied her up with my ties, ruining a few of them. I slapped her ass, squeezed her tits and fucked her relentlessly for half an hour straight. She had bruises and bite marks and red imprints the size of my hand all over her ass, tits and thighs, but no place anyone could see outside her clothes, just like we'd planned.

Then I got an idea. I laid her on her front and tied her hands behind her back. Then I blindfolded her and grabbed the lube. She started asking what I was up to when I dropped come coldish lube on her butthole. I grabbed her by the hair and with all my nerd aggression told her to shut the fuck up so I could fuck her ass. She started squirming in protest, but I wouldn't let her go and kept her pinned down. She started to scream, but I buried her face into the pillow until she gasped for air and I kept doing that until she'd stop screaming. Meanwhile, I was working my dick into her asshole. She started saying all kinds of words I couldn't make out through the pillow, but it didn't matter. I couldn't believe how turned on I was, but I wasn't gonna stop no matter what she said. When I finally worked my dick into her ass she screamed louder than ever.

I could have been tender. I could have been careful. Shit, i could have stopped. But I wasn't having any of that. I fucked her ass ruthlessly for a few minutes, muttering insults into her ear as I lay on top of her. I even called her racial shit like 'white slut' and 'my caucasion whore' and other goofy shit like that. All the while she screamed and screamed. Suddenly, her body stiffened and a scream caught in her throat, then she fell limp. I was genuinely freaked this time and for a second I thought maybe I'd hurt her. Then I remembered what I was doing and finished fucking her ass by cumming as deep into it as I could. During those last few pumps though, she didn't scream anymore.

After I rolled off her and untied her she slowly, carefully, rolled off the bed, grabbed her phone and wobbled to the bathroom where she stayed for what felt like forever. I figured she would tell her dad after I had to take her to the hospital for breaking her ass. I figured I was going to jail for rape. I didn't even try to fight it. I just waited for her to come back out.

When she came out she just looked at me for a minute in the doorway. Then she came to the bed, laid her head in my lap and sighed while she continued to check messages on her phone. I let her lay there for a minute before I went to the bathroom myself to wash up some. When I came back and sat down next to her she laid her head in my lap and kissed my knees, then my thighs, then my dick. Then she fell asleep.

I woke her up a couple hours later so I could take her home and that's when we talked. No one had ever fucked her ass before and she hadn't even considered the possibility of me wanting to until I lubed her ass. I'd been wrong to assume it was on the table and she'd been trying to stop me by saying the safeword, but she couldn't remember it so she'd been yelling the name of parks, cities, states and anything else she could remember to try and remember the safeword. I told her that even though she'd been yelling that stuff, I'd heard none of it I was so filled with lust.

What she said next turned my world upside down and ruined me for regular sex ever since. After the first few minutes she was in pain, but somehow she'd been turned on the whole time. Unsure if it was my force or the bondage or the anal sex or some combination of them, she started cumming. The last and biggest orgasm was when she'd stiffened up and damn near passed out. Although I had, essentially, raped her, she'd enjoyed it, despite having to wipe up a little blood when she went to the bathroom. Even so, she wanted to make sure that next time we had a proper safe word and protocol in place just in case next time she was genuinely hurt.

From that day and for the next nine months on until we broke up I did some of the most depraved things I've ever done with a woman and we had a blast doing them. After a year she dumped me for a wealthy friend of the family. I missed the sex, but had so many pics and videos from our adventures that I still got to fap to our shit afterwards. Then, two years later she reached out to me through facebook. Apparently, her husband was a shit lay who liked his sex very vanilla. I pissed in her face that night and have been more relentlessly brutal with her than I ever was before and she loves every minute of it while we call each other all kinds of racial shit. We've been hooking up at least once a month since. She explains away her bruises and red stripes left by my hands, belts and restraint implements as an aggressive boot camp aerobics class. Whatever. He married her, but she's still my bitch.