Freddie Gives Gayle Anal

"Hi, Freddie."

"Oh, hi Vinnie."

"What's wrong? You look down in the dumps."

"I'm stuck writing a story."

"You? Stuck? Are you kidding me? You've written a million stories already. You've written so many stories that I can't keep up with you. It makes my head hurt to read that much. Besides, I had to take a break because my finger is blistered from going across so many pages and my lips are tired from moving that much."

"Yeah, well, I need an anal story and I've never had anal sex."

"Taking it up the ass or giving it up the ass?"

"Giving it up the ass."

"Well, you know, I offered to fix you up with James, the guy who I was in the joint with that time but—"

"I'm not gay, Vinnie."

"Well, I'm not either, Freddie, but when there are no broads around you make do with what you have in front of you, if you know what I mean."

"Yeah, unfortunately, I do and that was an image that I really didn't need to have again."

"Didn't we have this conversation a couple weeks ago when you were writing your New Year's Eve Resolution story #2 about anal sex?"

"Yeah, but they put that story in non-erotic category?"

"Non-erotic? How was non-erotic about that story? We talked about all kinds of anal sex in that story."

"Yeah, well, that's the point. They don't want me talking about it. They want me doing it."

"Gotcha," said Vinnie putting a finger to his lip. "So, let's figure out how to get you to do it." He turned to me. "You know, Gayle would do you."

"Gayle?"

"Yeah, that woman who you ran away from in your story, Freddie Decides to Finally Try Anal Sex."

"Oh, Gayle, the librarian?"

"Yeah."

"Well, she's not bad looking and if my choices are doing your cellmate James or hooking up with a prostitute, I'd rather do the Gayle."

"I'll give her a jingle."

"Hey, Gayle, how you doin'?" Vinnie turned and gave me a look with a shrug. "It's me, Vinnie. Listen, my friend, Freddie, needs you to do him a favor. You know him already. Yeah, he's a friend of mine. You met him before. 'Member, you chased him down the street when he was asking about some anal literature from the library. Yeah, that's him. Well, I don't know about him being cute, Gayle, he just looks like a guy to me, but if you say he's cute, then that's between you and him. Tonight? What time? Okay, he'll be there. Yeah, I know where it is. I'll give him directions. Bye Gayle. Me? No, uhm, I have a wife and a steady girlfriend. Thanks anyway, but, uhm, maybe I'll stop by for a drink."

"So, what did she say, Vinnie?"

"You're on for tonight, 9 pm. Don't be late. And bring her some flowers. She likes the colorful flowers, you know, the bouquets."

"Yeah, okay, so where do I meet her?"

"She lives at the Riverview condos, 6B. Got that?"

"Yeah, 6B at Riverview."

"You got protection?"

"Protection? Gees, Vinnie, do I need protection from her? Oh, God, she's not into rough sex is she? She's not a dominatrix is she?"

"Nah, not that kind of protection," said Vinnie stuffing a condom in my hand, "this kind of protection."

"Oh, yeah, sure, of course. What the Hell was I thinking? Thanks Vinnie."

That night I arrived at Gayle's condo with flowers and a bottle of Jack. She opened the door as soon as I rang her bell. She must have been standing behind the door peeping through the peephole she pulled open that door so fast. I was nervous.

"Hi, you must be Freddie."

"And you are Gayle. I remember you from the library."

"You are quite the athlete. I never saw anyone run away that fast."

"Yeah, well, you know, I'm sorry. I was just uncomfortable with the whole thing."

"Are those flowers for me?"

"Yes," I said handing her the bouquet.

"And you brought some Jack Daniels, I see," she said with a laugh. "You won't have to get me drunk to hump my brown hole with your Italian salami," she said reaching down and feeling me through my pants.

"Yeah, but it think I will have to be drunk to hump...what did you call it a brown hole? Oh, God, with my Italian salami. You know, Gayle, it would help if you refrained from using such sexually offensive metaphors."

"Suit yourself, Freddie, I just thought a bit of pillow talk would get you in the mood."

"Yes, that and the threat of death."

"What was that?"

"Oh, I said that is the best part yet, pillow talk, I mean."

Gayle was wearing a mint green nightgown that was practically see-through. Definitely, I could see the outline of her B cup breasts, erect nipples, trimmed pussy, and the deep, dark crevice of her ass. In my nervousness and apprehension, her brown hole loomed larger and browner in my imagination.

"Why don't we have a drink to relax?"

I got up and poured her two fingers in a glass and filled the water glass to the brim with bourbon for myself. Once I started drinking my second water glass of bourbon, Gayle was looking kind of sexy and not all that bad looking. Her brown hole was not even on my mind.

We retired to the bedroom where she helped me remove my clothes. In one quick overhead pull, she was already naked. Fortunately, my cock was sticking straight out. I was hoping that the bourbon would postpone our anal sex by making Freddie, Jr. sleepy, but he was ready.

She took me in her mouth to make sure I was good and hard before slipping on condom on my cock. Then, she lubed her ass with some slimy gel and reclined on her side with her ass poised and ready for penetration.

"Don't worry, big boy, I'll be gentle," she said. She took control of me with her hand and gently eased me inside her anal cavity. It felt tighter than what I normally was accustomed to when having sexual intercourse with a woman's pussy, but this wasn't bad so far. It was only when she started humping me that I felt a bit of discomfort and the head of my penis hurt a little. Still, it was enjoyable.

I was even getting into it a bit more by feeling her big ass and slapping her round rump. My favorite part was reaching around her and feeling her tits. It felt good to take one in each hand as I humped her.

I apologize for being somewhat clinical in my description of my first time having anal sex with Gayle and it's something that I'm glad I did it to know that I will never do it again. I'm just not an anal type of guy.