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First Time Anal

She felt like a dirty, dirty girl – and loved it.
First Time Anal

One night my boyfriend came over and we were doing all the usual stuff. A little bit of missionary, I got on top, a bump or two of doggie style. All the right moves were being made because we’ve got that rhythm now; however, something made me decide to throw an added bonus on the table.

“So… you’ve been saying you wanted to go back door?” I asked with smooth feathers; I was chill.

“Yeah… yeah… are you interested?” he asked looking shocked, totally disbelieving that anything would happen.

“Sure,” I said with an added nod of the head.

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“When were you thinking?” he asked, “Were… were you thinking now?” He pointed to the bed, which we were already naked on, as in here and now.

“Is there a better time?” I replied.


This is how I do business a lot of the time. If I am given too much time to think it will be a no-go. Not that I ever condone force or being pressured into having sex, but I do think that when you want to try something you have got to decide, and then run into it not looking back.

“Well that’d be great,” he said, still looking very unsure that this is really going down.

“Cool,” I said with a thin, stretched smile and apprehension in my eyes.

More silence.

“Alright, well if we are going to do this there is going to be a preview with my fingers. We are going to have to warm things up first.”

I leaned over to the nightstand and pulled out a packet of K-Y Jelly that I had stumbled across in a magazine. It had been one of those women’s fashion mags, not Vogue or anything (they only have rich, crap smelling perfume samples), but more likely I got it out of Cosmo. Ah, Cosmo. Turning young girls into sexually liberated women by giving them the means to take it up the ass. In hindsight, none of this experience would have happened without this sample, so I would like to give a shout out to K-Y and Cosmo. Holla!!

I passed him the packet and he was beginning to beam. This was looking like reality. He put the packet on the nightstand and kissed me. I decided to go along with the events I had set in motion so I tried to relax. We made out for a while and then he rubbed my clit. Now this is money for me. I know it is different for every woman. Some are all about their tits. Suck on one of those and they are goners. Tidal wave. Not me however, I am all about the magic button in my shorts.

So he stoked me and I got crazy wet. Good times were being had by all, when I felt a questioning finger slipping down from my cunt to the awaiting chocolate starfish. There it was, the first wave of attack on what had to be the tightest anus in all 13 provinces. He scoped the surroundings and checked out the entry point.

I could just picture him reporting in the status. Sir, it is looking mighty tight. The guard is up. We may need some sort of distraction if we are going to take this ass tonight.

He pressed inside. I lay there trying to be as ass-tastic as possible. I took a deep breath and let it out.

“Um, just try and relax,” he said. He was patting my hair with his free hand like I was his faithful companion. It didn’t hurt; it felt wrong. I was struggling to wrap my brain around the fact that this wasn’t just an out-hole. People have been putting things up their assholes for pleasure purposes for a long, long time. This was a good distraction point to ponder, and he went back to eating me out, so soon enough I was feeling warm and fuzzy.

His warm, wet tongue was sliding along my sex from one end of the slit to the other, and then lower.

“Hello!” I said.

“Hello,” he said as he laughed at me.

“Oh sorry, I just wasn’t expecting that,” I eked out.

I laid my head back on the pillow and went back to working his digit in and out of my ass. There were moments were I could see how this could feel good, particularly combined with the nasty way he rubbed his tongue over my love dial. The charges coming off my clit were off the charts. As my breathing turned into a pant, he took another finger and started to really work my ass.

Now this kind of hurt, more like a twinge of discomfort, and I am not into pain. I made him stop. He leaned up to kiss me.

I shrank back in fear and stammered out, “don’t even think of kissing me when you were licking my poo hole!”

“Geez, you are just about the sweetest gal around,” he sighed.

“Sorry, but that doesn’t seem so romantic,” I said. I leaned into him and ruffled his hair. I kissed his neck, licked his earlobes (personal favorite), and ran my tongue all over his face. I enjoy being silly in bed, and he is always receptive to me nibbling on him like a small, wild animal.

We rolled around for a bit until I was straddling him. He went back to work. One finger seemed to be going in easy peasy, but two was still a bit much.

“I want you to really relax,” he said, “just try a bit more because we can’t get me in there if we can’t do two fingers.”

Notice, the “we” usage, “if we can’t do two fingers”, but we aren’t doing two fingers. I’m the one with his manly sausage fingers in my anus. I reminded myself that I had been the one wanting to experiment. Actually, I had wanted to try anal sex for years. I concentrated on relaxing my entire body from my toes to my nose. I focused on getting my body into a jelly state, and voila it worked. There he was kissing my belly, rubbing his cheek to the soft rounded flesh of my tummy, and his fingers were inside my chocolate starfish. It could almost be described as pleasant. Sometimes he pushed deep and that didn’t feel so good, but when it was just probing it felt good. I was beginning to feel like a dirty, dirty girl and I loved it. I never thought I would be the type of woman to enjoy a finger in the ass.

“So this is feeling about right,” he said with a question in his voice.

“Okay, so onto phase two then,” I said.

He nodded. I nodded.

“Flip over onto your stomach,” he cooed as he rolled me over.

I lay there and I made myself go limp. I kept thinking rag doll, rag doll, be a rag doll. You are loose and open. Go with it. I could feel his thighs against mine as he lowered himself onto my back. He started giving me kisses on the nape. He knows that this makes me butter, and I love him for knowing that. Slowly, he spread my cheeks, squirted K-Y all around, and began to rub the tip of his cock against my anus.

I felt him penetrate and surprisingly he didn’t feel so hard. I guess my sphincter is tighter and firmer than his cock. I almost wondered if it would hurt him if I gave a clamp down on his cock, but I was worried it would hurt me too. He worked his way in and out very slowly. It felt strange. This was much more invasive than a man being in my cunt because, I couldn’t see him and my butt felt so fragile. For such a tough, hardworking orifice it is astonishingly delicate on the inside.

We kept this up gently for a time until he started pressing a bit further than comfort would permit. We took a break and went back to other fun business. Then we tried it again. This went on for a while, until I told him I was ready to give it a rest. He kept going for a couple of strokes and then unloaded himself onto my ass.

This wasn’t exactly how I imagined it would go, but overall it wasn’t nearly as creepy and painful as I had heard; however, I wasn’t having any anal orgasms right off the bat either. I’ll have to give it a try again. Sometime. Maybe…


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