Soft First Date: 3

Book:Crazy Pleasure (Erotica) Published:2025-2-5

“No,” she said, shaking her head. “I want to fuck you.” As she spoke, she wiggled her fingers for emphasis. “I want to put on my strap-on dildo, and fuck you up your ass.” She let the words just hang there. They snapped me awake from the dizzying sexual feelings instantly. Instantly, everything had flipped 180 degrees. I realized I was lying down, legs spread and feet up in the air, with fingers up my ass. She wasn’t a slut. I realized she had intended this all along to work me towards this moment. I was to be the slut. I felt vulnerable and exposed and shocked, and her lascivious face was too close to mine.
“I can’t,” I said lamely.
“Yes, you can. You already are. Or doesn’t this feel good?” She waggled her fingers again.
“I guess, yeah.”
“You’ll have the best orgasm you’ve ever had.” Based on what I’d already felt, that might well be true.
“I don’t know…”
“Trust me, please.” Her expression had softened. I relaxed a little. This wasn’t some getting-even-with-all-men thing. I mean, this was still fucking bizarre, and I had only known her for a few hours, but for some reason I did trust her. I felt my resolve melt a little. Somewhere, in the far back of my mind, I heard my ex-girlfriend saying that I wasn’t much of a man, anyway. I thought, Fuck you, maybe someone likes me just how I am.
“Alright,” I said softly.
She broke out in a huge grin. “You won’t regret it, baby. I’m going to make you cum so hard. I’ll be right back.” She grabbed her purse and skipped down the hallway to the bathroom. The light flickered on, and the door closed. I sat up on the couch, smearing my wet bottom all over the leather. It felt so strange. What the hell was I about to do? I was more nervous than I’d ever been before sex. Even my first time, I was nervous, but not like this. I heard the bathroom door close, and I looked up. She stood at the door to the room, almost totally naked. I saw her beautiful breasts for the first time. My eyes hesitantly roamed lower. The harness looked like leather panties. There, like a lighthouse on an island, was her dildo. It looked like a real dick. I was terrified but I couldn’t look away.
“Megan, you’re beautiful.”
“You’re pretty damn hot, too.” She walked over and sat next to me. The dildo pointed up out of her crotch. I stared at it. Up close, I could tell it was a dildo, although it had a realistic shape. It looked huge. “Do you like it?” she asked, giving it a playful stroke.
“Can you feel anything?”
“Not directly, no. But there’s a second dildo inside that rubs me just fine when I move. Speaking of moves…” She leaned over and kissed me deeply. I realized that I didn’t need to take any initiative tonight. Her hand was pinching my nipple. Soon, she was pushing me over, and I put my head on the armrest. “Baby, this is only going to work if you spread your legs.” I complied, and she nestled tighter on top of me. Her hand was instantly at my asshole, fingering me again. I moaned in surprise. “Yeah, that’s it. Show me how much you enjoy it.” She reached down to her purse for lube and started to lube up her dildo.
Oh, what was I about to do? “Put your legs up.” I lifted them again. I felt the head of the dildo at my back door. “Relax, baby. This will only sting for a second.” And with that, she gave a good push, and it popped in. It did hurt, and I winced. “Relax. Breathe. Just let your body get used to it.” I tried to think about anything besides the fact that a dildo was going up my ass. In a few moments, it did stop smarting. All that was left was a pleasant feeling of fullness. “Are you ready for more?” I nodded, and she slid more in. It felt like I couldn’t possible take any more, but it kept going. Then I felt her crotch grind against my butt.
“That’s it. You’ve taken the whole thing.” I felt a little proud, and I smiled. “Now,” she said, “I’m going to pound your ass. I’m going to fuck you senseless.” With that, she gave a big, slow thrust. I gasped.
“Feels good, doesn’t it?”
“Oh, fuck, I had no idea,” I said breathlessly. She kept up a steady rhythm. Each stroke sparked a shower of sensations in my body.
“Wrap your legs around my back.” I did. “Does that feel any different?”
“Not really.”
“How about this?” She changed her angle.
“Oh my god.” It made my eyes roll back; it felt so good.
“Oh yeah?” She picked up the pace. Her strokes were faster and harder. I was delirious. I was moaning. I started bucking my hips up to match her thrusts. I wanted to feel the dildo as deeply as possible. I could feel her dildo deep inside me, opening me up. I put my hands on her butt.
“Fuck, fuck. Megan. Fuck me. Oh, fuck me harder, Megan.” She speeded up, pounding away at me. I was so close. I arched my back and pulled her even deeper into me with my legs. She slowed down, teasing me, until one long, perfectly timed slow stroke pushed me over the edge. “Oh, damn, I’m coming.” I felt my asshole contract on her dildo, and I spurted all over my chest. I nearly blacked out. It was the best orgasm of my life. Thirty seconds later, I was still coming down. My legs were trembling. “Oh, damn, I’m sorry,” I said.
“For what?”
“For coming so quickly. You didn’t come yet, did you?”
“No,” she said, and then she smiled. “We’re not done yet. On your hands and knees.” I could get used to this.