My friend Tracy came over to see me, telling me she desperately needed my help. It was about her new boyfriend, Drew.
“What’s the problem?” I asked.
“Okay, so the sex with Drew has been great. No complaints at all. Huge dick.” she started. I nodded. It did sound good so far. “The thing is… he wants to fuck my ass.”
“Okay…” I said. “And, you don’t want to?”
“I do want to,” she said, “I have never done it before. I don’t want him to know that. I want him to think I know what I’m doing.”
“Do you want me to give you some pointers?” I asked.
“No. I want to practice.” she reached into her tote bag and pulled out a huge strap on. It must have been over 10 inches and very thick. It was neon green, hideous yet beautiful. I took it and examined it.
“He’s about this big?” I asked.
“Maybe even bigger. But that’s the biggest one I found at the adult store.” she explained.
I took her hand and led her upstairs. I closed my bedroom door and started to undress.
“Get your clothes off and let me lube this bad boy up!” I said. She obediently removed her clothes and watched as I put on the strap on and lubed it, holding it in my hand.
“I like having such a big dick.” I remarked. I walked over to where she was sitting on the bed and turned her over. “Get on your knees, bitch. There will be no romance here. Let’s pop your ass cherry and get you ready for Drew.”
She laughed and got on all fours. Her asshole looked very tight and I pushed my thumb against it. She tightened up and moved away from me a little.
“Relax!” I said. She took a deep breath.
“It’s hard.” she whispered. “I’ll try.”
I grabbed her hips and pulled her towards me. I took my neon green cock and rubbed the head along her ass crack. She started to move her hips around a little.
“There you go…” I encouraged. I took the head and pressed it against her brown eye. She tensed up again. Slowly, I pushed the head inside of her and she gasped and pulled away.
“You’re going to give me blue balls here!” I said. I grabbed her hips again, a bit more forcefully now and held her in place. “Don’t move.” I commanded. I heard her panting; she seemed really afraid. Every time I started to push my cock into her, she tensed up and moved away.
I got it in about an inch and she cried out in pain. “I don’t think I can do this…” she said, sounding like she was going to cry.
“Look, girl, it doesn’t have to be so painful. Relax. But more importantly… as soon as you feel me going inside you, just push. Like if you’re pushing my cock out.”
“Push it out? Seriously?” she asked.
“Yeah. Like if you’re taking a dump!” I said and we laughed together. “Just push as I push and it will be easy peasy. Ready?”
“Ready!” she said. I pressed my cock into her ass and slowly pushed it in. She took a deep breath and started pushing against me and I slid into her, an inch at a time until half of my cock was inside her. She was whimpering a bit and I asked her if she was okay.
“Yes! I’m fine. Keep going.” she said, moving her hips around.
I pushed it in until I was as deep as I could go and then I started to fuck her slowly. She backed into me and started to really fuck me back. I picked up my tempo and started to ram a bit harder into her. She started to rub her pussy and moaned as she took her very first ass pounding. She made herself cum on her hand and then I slowly pulled my cock out of her.
“How was that? Do you think you’re ready?” I asked.
“Yeah, I think so!” she smiled as she collapsed on the bed. “That felt really amazing!”
“Good. I have a suggestion, though.” I said, glancing down at my dick. “Before you let him fuck you, give yourself an enema!”
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