First Time Anal With My Best Friend

My best friend Andrea and I were always very close to each other. We always tell each other about all of our relationships. We give each other relationship advice, we tell each other about every guy we fuck and we actually go into exquisite details.

So, one day we were just going about our usual conversations and I've got to say, Andrea is quite the little slut. I'm a year older than her. I've graduated college but she's still in in college.

Anyways, we were discussing all of our weird fetishes when she started telling me about the first time she had anal. Yes, the "first time". The way she described it, I have to admit, I sort of wanted to experience it.

"I thought he was going to put his dick in my pussy, but instead, he shoved it right up my ass. And it was the most painful thing I've ever experienced.” she told me.

"So, did you let him continue?"

"Of course, I did. It hurt like shit but it made me cum so bad."

And, at that point I started getting jealous.

I sort of whispered, "Well, I've never had anal before."

Andrea giggled, "Well, do you want to?"

"Fuck yeah", I replied without hesitation.

She leaned in and kissed me. "Wait right here".

She walked out and a couple of minutes later she came back with this bottle of tequila.

And, she didn't need to elaborate. We did a few tequila shots.

She always knows how to turn me on. She takes off her top and does a little striptease. Then, she kisses me while unbuttoning my clothes then gently kisses her way down to my pussy. She knows this better than most guys I've fucked.

Once we were down to bare skin, she told me to flip over and I did. Remember that wine bottle? Well, it probably gives better anal than any guy's dick. She slowly pushed the bottle in my ass. I gave out a gasp.

I was expecting pain, but this wasn't how much I was used to enduring. The first inch tingled, but once the bottle went in a tiny bit further, it was like someone shoved a foot ball right up my butt. I was literally screaming and Andrea was giggling because she knew I loved it.

She didn't go far into my ass. She took it out and I literally felt my asshole go back down to its normal size.

We tried a few more times and it was really painful but Andrea was rubbing my clit at the same time and the mix of pain and pleasure made me cum really hard. What I do it again.  Hell yeah!