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I’d been after my girlfriend to have anal sex for months but she always turned me down – at least a dozen times. I guess the pressure was kinda getting to her because she told me she wanted to “take some time off.” That’s girl talk for, “I’m breaking up with you but I’m too chicken to do it properly.”
Well, I’ll be damned if not even a week later her best friend didn’t come to see me. Kathy had hung out with us lots and I’d always admired her hot little body. She was really cute and always wore clothes that showed off her figure.
She came into my place and told me how sorry she was that Brenda had broken up with me because she wouldn’t see me as often. Then, we chatted for awhile. Finally, she got to the point of why she was really there.
“You know, Brenda told me why you guys broke up.”
“Ya – you must think I’m a real ass.”
“No. I actually didn’t get it. I told her she should try it.”
“Ya? You ever tried it?”
She shook her head. “No. Remember when I was going out with that guy, Mike? I tried to get him to go there but he said anal sex was for fags.”
My dick was starting to get hard just knowing that she was into anal sex and actually wanted it.
“He’s an idiot.”
“Ya.”

She was quiet for a moment. Then she said, “But you know, since we’re both single…”
“What about Brenda?”
She smirked and came over and straddled my lap.
“I won’t tell if you don’t tell.”
“Not a word,” I promised as she slid her top over her head.My hands went to those hot little tits right away. She was smaller than Brenda but who gave a shit – she was going to let me have anal sex with her!
I started sucking at her nipples and she got really squirmy on my lap, rubbing herself against my dick, which of course was rock hard by now.
I figured she was ready to get naked by now so I said, “C’mon. Let’s go into the bedroom.” She didn’t make any complaints and headed down the hall right away. Guess she wanted it as badly as I did.
She quickly removed her clothes and started to work on my cock. First a little hand work and then she started sucking. Her ass and pussy were right in front of my face so I started to finger her. She was already dripping wet and I had no problem sliding a couple fingers in there. She moaned with her mouth full of my dick so I added another one. She was moving back and forth over my hand and it looked great but I was watching her puckered hole. I brought my thumb up and started to rub it.
“Wait…”
Shit, I thought, she’s chickening out. No anal sex for me. But she wasn’t. She reached over to the side of the bed where she’d dropped her purse. She came back with a little bottle of lube.
“Use this,” she said and went back to sucking my cock. So, I squirted a healthy amount over her little rosebud, slid my finger back into her cunt and popped my thumb into her ass.
She muttered something over my cock but it didn’t sound like “stop” so I kept going. I pumped away at her juicy twat and her lubed up ass until I couldn’t stand it anymore.

“Kathy, c’mon. I’m going to cum and I want to get inside your ass.”
She sat up and smiled at me. Grabbing a condom from my bedside drawer, I slid it over my cock. I was hoping I’d last long enough to really enjoy it.
Kathy got on all fours in front of me and said, “Just remember to go slow ok?”
I slid into her pussy first. It felt damned good but I didn’t want to waste too much time there so I headed for the back door. I pressed the head against her tight ring and at first it wouldn’t give.
“Push harder,” she said.
I did and it was almost like a pop. She grunted really loudly, but she didn’t’ tell me to stop. I slid in a little more. Fuck, her ass was tight. With each stroke, I thrust a little deeper, a little harder. I couldn’t believe I was finally fulfilling my anal sex fantasy. Her hand moved to her clit and began to rub. Although her face was buried in the pillow I was pretty sure I could hear her say, “Yes, yes…” and “Fuck…” over and over again. Pretty soon she was backing her ass up against my cock. I knew I couldn’t hold back for much longer so I was really glad when her body started shaking and her muscles started to clench around me. It was the greatest thing I’d ever felt. I kept pumping away into that hot tight space until I came harder than I had ever cum before.
Finally, I let my cock slide from her ass and we both collapsed.
“Promise you won’t tell Brenda that we had anal sex?”
I laughed. “Brenda who?”
She smiled. “Does that mean we can do it again?”