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Erotica: My First Anal Experience

Erotica: My First Anal Experience

You never get to grow unless you take chances, right?

Tom has always been willing to talk about all of my desires, regardless how silly or kinky. While not all of them have worked out and we end up a tangle of laughter and lube, he’s always willing to discuss and try whatever I dream up.

When I told him I had something new to try together, his eyes lit up. I don’t know why I was nervous this time, what I was about to ask for isn’t a very shocking act these days. People are doing it all the time! But I had to steel myself with a deep breath before asking:

“Tom, will you please fuck my ass?”

His face spread in a delicious smile and we launched into a deep discussion of my assplay experience (which is none). He shared his own enjoyment of bum fun and guided me through how he thought the whole, sexy situation should happen. It all sounded so hot and I was squirming in my seat. I could tell that my pussy was completely wet. But we agreed that tonight would be the night I popped my anal cherry.

* * *

I could hardly wait. I had so many sexy fantasies throughout the day. It felt like cum was dripping down my legs all day while I tried to work. It was not a very productive day, except in my fantasties.

When Tom arrived home, I greeted him in my bathrobe and handed him his. He stripped down and we ate a delicious, light meal. The conversation naturally swapped to the evening’s upcoming plans and I was squirming all over again. Tom’s cock was also stirring under his robe and I could barely contain myself. After the food was done, I took Tom to our bathroom and turned on the shower.

Water has never felt so good. Soap has never been so soothing. We kissed deeply under the streams as we rinsed the heat of the day off our bodies. Were it not for the greater plan, I’d have begged for Tom to slip his meat into me right there. But I wanted more.

Tom turned off the tap and I was dripping in every sense of the word. I practically ran to the bedroom and flopped myself down, ass up, on the bed. Tom finally made his way in, building the suspense, to find my butt in the air and my soaking pussy spread.

He reminded me that we were going to start with a body massage, but I begged for more, now. When his thumb grazed my clit and his tongue first touched my ass, bolts of sexual energy flew through my body. Tom later recalled that my moan was the loudest and deepest he’d ever heard. I can’t even remember, the pleasure was so intense.

I do remember, however, looking back at Tom as he began licking my anus and stroking my clit in earnest. He looked so intense and passionate about what he was doing. That just pushed me further along. Every lick of his tongue against my sensitive little hole was pure bliss. I could have my ass eaten for hours, especially with Tom fingering me.

WIth one long, flat swipe across my hole, Tom pulled away slightly. I was open and exposed on the bed waiting for what was next. After what seemed like hours, Tom’s hand returned to my vulva just as he spread some slightly cool lube all over my ass. Fortunately, it warmed to my skin almost instantly as he massaged it all around my waiting hole. It felt so good!

As I absorbed this new sensation, Tom’s finger slowly and patiently easing my anus up, I came for the first time. Just as he was dipping the tip of his finger inside me, my body exploded in pleasure. Tom held tight and I felt my ass tensing and pulsing on his digit. Just as I was easing down from that hot cum, as soon as my body began to loosen again, I felt the most fulfilling sensation of my life. Tom slipped his finger right into my ass.

I can barely describe the feeling of fullness and satisfaction I felt at that moment. As he worked his finger deep inside me, my body was still and transfixed. He, literally, opened my body to a new world, and I knew I’d never forget this moment.

Slowly, Tom pumped his finger in and out of my ass. I gasped when he slid another from his other hand into my cunt. I was panting hard with pleasure into the mattress. But I muster some breath. I needed more.

“Tom, please,” I whispered. “Please fuck my ass.”

I didn't look, but I could tell he was smiling. Slowly he pulled his fingers out of me. I heard him squeezing lube from the bottle. He coated his cock in it.

And then I felt it. I felt his penis pressing against my asshole. Time seemed to stand still as he pushed so damn slowly into me. I felt my body widen to accept him. I also felt another orgasm growing inside me. That delicious head carried on, penetrating my tight ass. I was in heaven.

When his cock head pushed in with a little pop, I nearly lost my mind. It hurt a little, so Tom stood still to let me adjust. It didn't take long before I was easing my bum back against him. My tight ring started to slide more easily down his shaft until my ass fully engulfed his penis.

Somehow, I managed to transcend even heaven. Tom checked in to see if I was okay and all I could do was moan and nod. I could barely concentrate on holding my body up I was so taken over with pure pleasure. That orgasm that was waiting on the cusp of greatest began a slow unravelling as Tom began pumping in and out of me. Each stroked nudge me closer and closer. Feeling his dick slide in and out of my ass so effortlessly was pure sex magic.

And that did it. My whole body began to tremble in pure Bliss as wave after wave of pleasure rolled through me. There was no holding back. Both my pussy and ass squeezed and contracted over and over.

And that did it for Tom. I felt him give one harder push, almost knocking me over in my orgasmic state, and then he growled in pleasure. It felt just slightly different as he filled my ass with spurt after spurt of hot cum. And I revelled in it. This was the most intense sexual experience of my life.

Tom slipped out of me and we both collapsed on the bed. I curled up next to him and, for the first time, realized that my bum felt just a little raw. But in the best possible way.

Tom checked in and we relived the whole experience. Were I not completely spent, I might have asked for more. But we decided to rest instead. With a great partner like Tom, my ass isn't going anywhere, there’s plenty of time for more.

About Jon Pressick
Jon Pressick

Jon Pressick is the sex community's international gadabout and Cherry Banana's writer in residence. An award-winning sex writer and blogger, Jon is the editor of the critically-acclaimed Best Sex Writing of the Year, Volume 1. He is a frequent contributor to Cherry Banana with a range of sex-related content and his writing has appeared in numerous magazines and books, as well as all across the Internet. Jon is also a co-host and producer of the long-running sex radio show Sex City. You can keep up with his many sex-related articles here at Cherry Banana or at his own blog, Sex in Words.

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