Tim: Anal Adventures

I had known for a while Wes was going away for work Tuesday night so I had already text Tim asking if he wanted to stay at mine the night (he actually ended up staying 2 days). Getting ready for the evening we had been texting lots more than usual; general flirting, sexts and nudes were exchanged and by the time Tuesday came around I was so fucking excited about seeing him!

In recent weeks Wes and I have been making more effort to include anal fucking in our sex life and it’s made me think about trying to have anal with Tim. In fact, I’ve not stopped thinking about it which has led to some very nice masturbation sessions. The problem here is, I know Tim has never had anal with anyone and obviously, because I’ve discussed it so much – he’s fucking huge! I’ve never had anything anywhere near as big as it in my ass and I was worried it wouldn’t work. But, the more I thought about it, the more turned on I became… I hadn’t discussed it with Tim at all so I just figured I would approach the conversation if I got a chance…

Tim arrived at my place early Tuesday evening wearing a white shirt and suit trousers – his suit trousers were loose fitting – I figure anything tighter and his trouser snake would definitely be visible… I was wearing a skimpy white tank top and a short, pleated skirt with a pair of high heels.

We sat on the sofa, drank some wine and had some shots. We were laughing lots and it was easy to tell Tim was so much more confident with me now. At one point I walked out of the room to get another bottle as I left I could feel his eyes on me so I quickly whipped up my dress to show him my bare ass. “Fuck” he shouted as I left the room. Although we were having loads of fun and flirting heavily at no point did I manage to discuss anal with him but ‘they’ll be other times’ I thought to myself…

At some point a slow song came on that I liked – I can’t honestly even remember what the song was. I invited him up to slow dance with me and begrudgingly he agreed. He put his arms around my waist and I moved as close to him a possible as we swayed to the music. He looked at me and kissed me – this was actually the first time Tim had ever made the first move on me, which I found really hot. As we were kissing our hands were wandering – his hands touching up my thighs, just underneath my dress. I put my hands on his and moved them up on to my booty. I kissed him harder and I felt his huge bulge poking at me from under his trousers. As we continued to kiss I unbuckled his belt and unbottoned his trousers. I pulled my lips away from his, and making sure I mad constant eye contact I really slowly moved down onto my knees in front of him. I pulled his trousers and boxers down which released his huge throbbing cock – pointing towards me I took hold of it and pulled it into my mouth. His pre-cum tasted amazing. After sucking him off for a little I looked up at him

“Lick my pussy Tim”

I got up and moved over to the sofa, sitting down and spreading my legs. He moved towards me, got down on his knees and fingered me while his tongue licked the length of my cunt. I came hard in under a minute.

“You ready to fuck me baby?” I asked.

“I can’t fucking wait” he told me.

I got up off the sofa and got on all fours on the floor. “Come fuck me please baby”

I felt him move up behind me, down on his knees and then I felt his massive monster cock enetering my soaking pussy. He was moaning loudly as his cock filled and stretched my pussy, and by the time he was completley inside me and had taken a hold of my hips I had already come again… “Please don’t stop” I pleaded and he kept pumping away – his balls slapping against me. I came again. This was the third time I had fucked Tim, and every time it just felt better and better.

“I want you in my ass” I told him as I was still recovering from my orgasm. The next thing I knew he had slid a finger inside my tight butt, it felt amazing, but it wasn’t what I wanted.

“I didn’t mean your finger” I told him, moaning away.

“What?” He asked?

“I want your dick in my ass”

“Really? Are you sure? I’ve never ummm I’ve never…”

“I know. I’m sure baby. I want your massive dick in my ass”

He pulled his finger out and I moved forward releasing his cock from my pussy.

He took hold of it and I used my one hand to stretch my ass cheeks apart.

“Just take it slowly” I told him. But oh fuck, I was ready for this! I wanted it so much.

He pushed his cock against my asshole. “Just push it in gently” I told him.

He did, and he only had half the tip of his cock inside me and I could already feel it stretching me. “Ahhhhhh” I cried out. It definitely hurt a little but also, it felt fucking incredible!

“Now a little further baby” He edged a little more in, but I knew he was too big for this position… “Hold on” I told him. I got up, sat on the very edge of the sofa and lifted my legs up high, parting them as much as I could. “Try this Tim.” He knelt in front of me and started edging his cock into my tight little hole. I put my arm around on his waist and I’d pull him towards me every time I knew I could take a little more of him. “Just gentle strokes” I would tell him. Edging him in a little more with each stroke. Before too long he was completley inside me and he felt fucking wonderful. “You feel amazing” he told me. “You too. Fuck. Ahhh”

“Just a little harder now please baby” he did exactly as I wished. I put my hand onto my pussy and started to rub my clit. I was so fucking wet. So fucking turned on. I couldn’t believe my tight, little asshole had taken all of him… I was getting more and more carried away and closer to cumming again with every hard, long stroke.

“Fuck my ass hard baby” I pleaded.

Tim has always been excellent and giving me what I need. He held onto my ass cheeks and fucked me hard. He fucked me, fucked me and then fucked me some more until I could take no more and came everywhere. My orgasm seemed to last an eternity. My fingers were furiously rubbing my pussy and has he drove extra deep into me I squirted everywhere. More than I have ever squirted before. It covered the floor, myself and Tim’s chest. Still catching my breath Tim pulled his monster cock out of me, stroked it’s massive length twice and absolutely covered me in cum. It was on my face, my stomach, my thighs and my pussy… I stuck my tongue out a little to grab and swallow a bit that had landed on my lips…

It was anal sex with the biggest cock I have ever seen or felt. It was fucking incredible. That night and the next we fucked lots more and I’ll probably write about it sometime, but there was something really fucking sexy about this. Tim had lost his anal virginity – and I’d always have that…

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