Part 2

Thursday December 22

I made preparations in the morning. After lunch I sat in my car near the Rivers’ house, killing time by tinkering with some code on my laptop. I had to keep the motor running to stay warm.

It was 4:00 when I got Becca’s message. I drove up the driveway and barged through their front door, which thankfully was unlocked, and I walked briskly into Becca’s room where Ethan was undressing. He was very surprised. Becca was sitting on the edge of the bed with her phone in her hand, trying to look busy.

“Get dressed, you’re coming with me,” I commanded him. “Bring a jacket. And a tie.” He looked at me with disbelief at first, but I raised a razor-sharp eyebrow at him and then he scurried off to his bedroom. I could smell the alcohol on his breath.

With Ethan gone from the room, I told Becca softly, “We’ll be back in a couple hours, ‘kay?” She shrugged.

When Ethan returned he was, as I had requested, dressed and wearing a jacket. Before he had been wearing a T-shirt, but I guess when I said tie, he assumed he needed a collared shirt, too. No matter. I grabbed the tie and lead him like a dog on a leash out to my car.

My knees nearly froze on the walk to my car. I have this knee-length trench coat - a gift from Oliver welcoming me to the world of private investigation. I was wearing that, and a hat that my aunt had given me last Christmas, and a scarf. Underneath the trench coat was ... not much. But the coat did a fine job of keeping me warm from the thighs up. My boots, which went up high on my calves, protected my feet just fine. But my knees were cold. My glasses threatened to steam up from the heat of my face, as well.

“Lexi, I...,” Ethan began once we were in my car. I slapped him.

“Looks like someone has forgotten the rules of this relationship,” I said authoritatively. “You will call me Miss Green.” I really was curious what he intended to say, but re-establishing our roles seemed more important.

We drove until we reached the sex toy store. All the kids at Saint Frances Prep had driven by it a hundred times. All the girls used to make lewd jokes and dares about the place, but I had never known anyone who had gone in. Leading Ethan by his Burberry leash, we went inside.

“Choose three,” I told him and let go of his tie.

“I don’t understand,” Ethan said. “Miss Green,” he added a beat later.

I spoke slowly and clearly: “Choose the three items in this store with which I’m going to fuck you.” The clerk and the other four shoppers almost certainly heard me, but they pretended they hadn’t.

It didn’t take Ethan very long at all to select our equipment. Back in high school, Ethan had frequently browsed sex toy websites - I knew because I spied on his browser history. I guess he had a pretty good idea of what was available.

The first pick was no surprise: a strap-on dildo. I’m glad he picked it, even though I had a better one back at my apartment. Wasteful, but I wasn’t going to make a four hour drive to pick mine up.

The second item didn’t surprise me either. It was a bondage kit: four padded cuffs and several velcro ties of varying lengths. The ideas were already flooding into my head.

Third was a pair of nipple clamps, with a chain between them and a bell hanging from each. That never would have occurred to me. I didn’t even know what they were for. But I had set the rules, so I wasn’t about to reverse my decision.

All told it set me back $130: a small price to pay if I can help whip Ethan’s life back into shape, but still not a bad investment even if all I get is a day of kinky sex with a cute guy.

Ethan looked so incredibly meek as I lead him like a dog to the counter to pay. I was wearing my best sinister smile. The clerk wasn’t showing any outward of judgment, but Ethan must have been horribly embarrassed.

The next stop was my parents’ house. It was a calculated risk: I was pretty sure that we’d be done before my parents got home. The other options would have been a hotel, or Ethan’s house. I figured a hotel would take too long, and I didn’t want Becca around while I fucked and humiliated her brother.

As soon as we were inside, I turned to face Ethan and I opened my jacket, revealing my lingerie. Not quickly, but not slowly, I shrugged the trench coat off of my shoulders and let it fall into my hand. From there it and my hat and scarf flew to the sofa.

Up top I was wearing a black lacy bandeau. Down below I had black panties with built in tiered ruffles. My left thigh was adorned with a garter. And of course, from the knees down, I was wearing black leather boots.

I poured myself a shot of whiskey, for warmth and courage, and downed it in one gulp. I offered one to Ethan but surprisingly, he refused.

I let Ethan stare at my ass while I found paper and a marker and crafted a do-not-disturb sign for my parents’ bedroom door, just in case. It would have to be my parents’ bedroom: my bed frame was completely ill-suited for bondage.

The real fun began when I tied Ethan up at the foot of the brass bed. Each hand was tied to a bedpost and each foot to the bed’s feet. His cock and balls were resting on the mattress, peeking through the bed frame’s vertical bars like a lonely prisoner.

I lounged on the bed in front of him, toying with his junk with my booted foot. He was completely hard. “Poor little guy,” I said about his dick. “So eager. But it will be a long time before he gets to play.”

I slipped out of my panties - awkwardly because I kept the boots on - and put on the strap-on harness. On my knees on the bed, I held the detached dildo to his mouth. “Suck it - get it good and wet,” I said. “You know, in a minute, you’re probably going to wish that one of the three items you picked out was a bottle of lube.”

Ethan dutifully covered the first three inches of the fake cock with as much spit as he could manage, and so I snapped it onto the harness before leaving the bed and taking position behind him. His breath was short and shallow as I wrapped my arms around him, touching his chest, brushing his nipples, while my plastic cock poked his thighs.

When I’d had enough foreplay, I covered the dildo with lube from the bottle I had bought this morning. I’m not a sadist. I stuck it in him and he moaned. It went in without much trouble, so I started stroking in and out of him by working my hips.

“You have an experienced ass, Ethan,” I remarked. “How many other people have fucked your ass?” Slow thrusts, with my arms wrapped around his chest for leverage.

He didn’t answer right away so I asked again, sternly: “How many?”

“Two, Miss Green,” Ethan said. His body was tensing up in time with my thrusts.

“Men or women?” I asked. The harness was giving my pussy a nice rub. I reached down to adjust a strap that was pinching me. I tried to give him a reach-around, but the bed frame didn’t really allow it.

“A man and a woman,” he answered. Surprising. “Well, a man and a ladyboy,” he corrected himself.

“Ladyboy, huh? Was she prettier than me?” I asked. I pulled almost all the way out to scout for a new position. I had been poking him pretty deeply, but I wanted to focus more on his prostate.

“No, Miss Green.”

“Was her dick as big as mine?” I asked. I rolled my hips and slid back in slowly, watching for the point at which he winced.

“No, Miss Green,” he said, and gritted his teeth. That was the spot.

I stood on my tip-toes and hammered him right in that spot. I gave him shallow strokes pushing hard against the wall of his rectum and into the delicate gland beyond it. “Did she fuck you as hard as I fuck you?” I asked, knowing that it was an unfair question.

“No, Miss Green. Oh god!”

I kept driving my artificial cock right against his come gland. His whole body was shaking. “Don’t do it - don’t come,” I warned him.

“I can’t help it - I can’t last!” He moaned.

I slowed down, dropped to flat feet. I gave him a couple deep cool-down thrusts. “I’m not ready for you to come yet,” I told him.

After a brief pause in the bathroom to clean the dildo, I came back to the bedroom with the harness and toy still attached. I felt up Ethan’s butt from behind. He was still tied up and helpless. “It’s a pity I can’t ejaculate,” I told him. “I would love for you to feel my hot semen dripping down your thigh. Did your ladyboy come in your ass?”

“Yes, Miss Green.”

“Ah. Well, that’s one she’s got over me,” I said.

I untied Ethan and retied him on the bed. He was lying on his back, with his arms tied to the center of the head board and his feet tied to the footboard. Then I set about the frustrating task of trying to attach the clips to his nipples. I spent minutes trying but I just couldn’t make them stay put. His nipples were so tiny! I wondered how anyone makes these things work.

Ethan was looking at me, trying to be patient but clearly wanting to say something. Eventually I gave up. “What?” I asked.

“I thought those would be for you, Miss Green,” he suggested meekly.

Duh! What the hell had I been thinking? I felt stupid, but I had to maintain a sense of control. “Well isn’t that presumptuous?” I said menacingly. “I’ll humor you - but it’s going to cost you.”

I took off my bra, wondering absently whether I had performed a Reddit-worthy boob drop. The clips attached to my nipples just fine. I expected them to hurt, but they didn’t.

I sat on the bed and idly fingered his now limp dick: the whole thing was covered with pre-come that had partly dried and become tacky. I teased his scrotum with my fingernails - nothing painful, just enough to trigger a reflex. I looked in his eyes. He really looked like he needed this. Or maybe that was just how I justified it to myself.

It was time to fuck, but at the last second I decided that regular cowgirl wasn’t exotic enough. Instead of leaving his feet tied to the footboard, I retied them to the headboard posts. Ethan’s knees were up against his chest and his feet in the air. For good measure, I put a strap around his waist tied to the footboard, to keep some tension on him. He looked very, very vulnerable.

Ethan’s dick tried to stay tucked between his thighs due to the angle of his hips, but I wasn’t having any of that: I pulled it back so that it was pointed straight up, ready for me to ride. I was worried that it might be uncomfortable for him, bent that far, but he didn’t say anything. Finally, I squatted down, sucking his cock into my cunt, until I was resting mostly on his thighs. My strap-on dildo was still attached to my body and pointing at his face.

“Shall we begin?” I asked. Ethan nodded.

At first I was upright, mostly sitting on his thighs but bouncing up and down for some short strokes. My own artificial dick was wobbling up and down in front of me putting intermittent pressure on my outer sex. The bells hanging from my nipples chimed pleasantly with my motion, their weight tugging on my nipples in a slightly disconcerting but certainly stimulating way. The sound reminded me of Christmas - jingle bells and all that. ‘Tis the season.