I’d been dating Lucy for a while. She’s sweet, simple, and a lot of fun. She’s got a body to die for, specifically an ass that makes people turn heads, though her breasts are on the smaller side. Personally, I think they’re perfect, but she always complained they should be bigger. If you ever wanted to see Lucy get mad, all you had to do was mention her chest. Even a compliment would get you a side-eye.

​In bed, she’s a ten. Pure fire. But she wouldn't go near anal sex, no matter how much I begged. If it were today, knowing what I know now, I would’ve let it go. But back then, I had a massive thing for it. I tried everything to convince her. I talked about it, I’d slip a finger in while we were busy to see if it sparked anything, but no luck.

​One day, we were in bed and I made the mistake of being too pushy about it. She jumped up and ran to the window. I tried to follow her, but she shot me down with a sharp, 'NO!' Short and blunt. I just sat there looking regretful while she stared out the window at the street below.

Then, she turned around and said, ​'I’ll do it on one condition.'

​'What?' I asked, hopeful.

​'If you let me do it to you first.'

​'Wait, what? Haha! How would you even do that?'

​'Yes or no, Marc?'

​'Fine!'

​'Fine, what?'

​'Fine, okay! Deal.'

​She gave me this wicked little smirk. I thought, Man, what is she up to? She grabbed her clothes and got dressed in a flash.

​'Stay here!'

​'Where are you going?'

​'Just wait for me, okay?'

​She left the bedroom, and I heard her grab my keys and slam the apartment door. Then it hit me. What was directly across the street from our building in Miami? A Boutique Erotica. If she was talking about 'doing me,' I knew exactly what she was buying. I sat on the bed with my head in my hands. I’d walked right into this one.

​To make matters worse, it wasn't just my ego at stake, it was my reputation. I knew the girls who worked at that shop. They knew Lucy was my girlfriend. They were going to see her walk in, buy a strap-on, and walk right back into my building. They’d know exactly where that thing was going. Plus, I shared the apartment with two other guys. One was away, thank God, but the other, the biggest jokester of the group, was probably asleep in the next room.

​Less than twenty minutes later, she was back. She walked in with a red bag and pulled the thing out to show me. A purple dildo attached to a harness. She stripped down and buckled it on while I sat there with a pillow over my lap, frozen.

​'So,' she giggled, 'are you going to get on all fours or what? Didn't you say it doesn't hurt? That I just need to relax and accept it?'

​My own words coming back to haunt me.

​'Fine. Let’s do it.'

​I got on all fours. The worst part was that she was talking loudly. I didn't know what my roommate was doing, but he was suspiciously quiet. Relax, man! Just relax! I thought. I actually managed to loosen up. It was the strangest feeling, having my own gear hanging there while I waited for a fake cock to enter me. I felt like I was betraying my own dick; I wanted to apologize to it. Then, I felt that cold, hard silicone push against me. I let out a small moan, more out of surprise than pain.

​'Is it hurting?' she asked.

​'No.'

​'Are you sure?'

​'Just get it over with!'

​Luckily, she’d bought a small one. She started thrusting: one, two, three, four, five times.

​'Wow, this is a workout!' she panted.

​She kept at it until I started feeling something... different. Worse yet, it was starting to feel good. Suddenly, I realized I was moaning like a woman, just in my deep, gravelly voice. It was totally involuntary. It was like she’d hit a 'play' button inside me. She stopped to check on me.

​'You okay back there?'

​'Oh, God... yeah.'

​I stood up, turned to her, and said, 'Okay, you’ve had your fun. Now it’s my turn.'

​Have you ever felt that surge of guilt when a girl looks at you like a lost puppy? She stood there, slowly unbuckling the harness with a sad look in her eyes. She turned around and got on all fours for me. I almost felt too bad to do it, but my wounded pride, and my slightly stretched-out rear, demanded justice. This was about revenge now.

​I grabbed the lube she’d used on me, slathered myself up, and pressed against her. She buried her face in the pillow, dead silent. But she was tensing up so hard I couldn't get in.

​'Relax, Lucy.'

​She finally let go, and I pushed the tip in slowly. She made a high-pitched 'hmmm' sound, gripping the sheets until the tip slipped out from the tension.

​'Easy... just breathe...'

​The second she relaxed again, I pushed back in. I went inch by inch until I was halfway, then all the way. She was frozen, her lungs working overtime but not making a sound. I pulled back gently and pushed in again. Nothing. I did it again, a bit faster. Then faster still. She stopped fighting it and started accepting the rhythm. Suddenly, I felt something wet splashing against my legs. She was absolutely soaking her front side.

​'Well, look at you!'

​I gave her ass a smack and grabbed her hair, pulling her head back. She started moaning non-stop, actually begging me to go faster. She was so tight I had to be careful not to overdo it. She grabbed my hips, but not to stop me, she was pulling me in deeper. She’d discovered the dark side, and she loved it. The headboard was banging violently against the wall. It didn't take long for me to finish.

​After she left, my roommate came out to grill me.

​'Man, I’ve never heard her scream like that! At first, I thought it was you moaning, but then I realized it was her voice!'

​She didn't take the toy with her when she went home. I didn't know what to do with it, so I shoved it under my bed. I forgot that my roommate had a dog that loved playing under there. It wasn't long before that purple thing was found shredded to bits in the middle of the living room. Surprisingly, nobody asked me what it was.

​But the kicker was a few days later. I ran into the girls from the sex shop at a Starbucks near my place. They were all sitting at a table while I was at the counter. I’d tried to hit on the cute redhead once, but she’d shot me down. That day, she looked at me with a wicked little smirk and gave me a wink. Then she whispered something to her friends, and they all burst out laughing.

​I’ve never wanted to disappear more in my entire life.