School Of Anal

We were on our third drink when the questions started. This was always the way with Sienna, a few cocktails and the ‘naughty’ inquisition began. I always thought it was funny that a few martinis could wash away her preconceptions but I guess that’s the way with anyone.

With Sienna though it always came down to the same line of questioning. Anal sex. I’d told her once that I was quite into it and since then it had become her favourite drunken conversation topic. Why did I like it? Does it hurt? Should she try it? etc etc. We were going out tonight and were waiting for our friend Cushla to arrive before we all hit the town but seeing as at the moment it was just the two of us in her apartment I didn’t mind talking with her about my obsession, it was only when we were out in public and she started on the topic that I got embarrassed, mainly because she was just so loud.

“So, tell me about it Portia.” Sienna giggled “Why do you like it so much?”

We’d had this conversation so many times before but as usual I humored her.

“I guess it’s just something I’ve always done, pretty much since I started having sex.” I started recalling to Sienna the story of my first time. “Remember me telling you about Hamish? He was the one that got me into it. He was a bit rough with me and I didn’t like it at first but after a few times I started to enjoy it. Since then I’ve done it with other guys who have been a lot more caring and taken their time rather than just shoving it in and that’s what has really turned me onto it. If a guy knows what he’s doing it can be really great.”

Sienna had a funny smirk on her face.

“What is it?” I asked.

“I’m just picturing you bent over on the back seat of Hamish’s mini minor taking it up the arse.” she replied.

“Shut up!” I teased, slapping her arm.

There was a slight pause, almost as though Sienna wanted to ask me something else but was too scared. I broke the silence. “So, you still haven’t done it?”

Sienna shook her head, “No, but I think I’d like to. It would have to be with the right person though you know? I don’t want to do it with someone I don’t trust.”

I nodded. There was another awkward pause. This time it was broken by Sienna.

“Maybe you could show me how to do it?” she suddenly blurted out.

I nearly dropped my drink. It was something we had joked about before when we were trashed but this time she almost sounded sincere.

“I mean, I trust you more than I do any guy I know and since you’ve done it so much I’m sure you would be the best person to show me how.”

I’d never done anything with another girl before, apart from a drunken snog, I was purely a guy only girl but I could imagine doing something with Sienna, she was quite beautiful afterall, not some butchy bull dyke, the guys certainly liked her. If I was going to be involved in any girl on girl activities it wouldn’t be hard imagining doing it with her.

I decided to call her bluff, to see if this was just another one of her games.

“Ok,” I said, turning to face her “We’ll do it. It will be like coaching or something.”

“Alright,” Sienna clapped her hands “Ooh I’m quite nervous but excited.”

The downstairs buzzer rang.

“That will be Cushla.” I said

“What should we say to her?” asked Sienna pressing the door access button “I don’t want to go out now, I want to do this.”

She sounded like a spoilt child that had had her favourite toy taken away.

“Wait!” She had suddenly hit upon an idea “We’ll ask her to train with us.”

“I don’t know Si, do you think she’ll be into it?” I asked worriedly.

“Only one way to find out.” replied Sienna bouncing up and down in excitement.

I was quite surprised to see her so enthusiastic about the whole idea.

There was a knock at the door and Sienna answered, a huge smile beaming on her face.

“Someone’s excited.” said Cushla as she walked in, tossing her bag on the couch.

“We’re not going out anymore.” Sienna began. “We’re staying in and having fun instead.”

“What? Why?” whined Cushla. She’d obviously gone to a lot of trouble to make herself up for the night.

“Portia is going to coach us.” Sienna huffed, as though it was so obvious.

Cushla was excusably confused. “Coach us, what are you talking about?”

“Portia is going to show us how to take it up the arse.” Sienna explained matter of factually.

“Right,” Cushla answered sarcastically. “Look, whatever you two want to do that’s fine, just count me out Ok?”

She got up to leave but Sienna grabbed her elbow.

“No, stay. It’s going to be fun. You can just sit and watch if you want, you don’t have to do anything.”

Cushla looked over at me suspiciously but I nodded back to her reassuringly and told to her to stay. She sat back down on the couch and didn’t say a word.

“Hang on, I’ll get some things” Sienna ran into her bedroom and returned with a couple of differently shaped and sized toys, a tube of KY jelly and some other paraphernalia and dumped them in Cushla’s lap.

“Yuk!” exclaimed Cushla throwing the toys onto the floor.