This Is A Great Story.

This is a great story.

FIRST-TIME ANAL STORIES, CHAPTER 5

Happy First-Time Friday, anal pervs! Here is the fifth installment of our First-Time Anal Stories series. This one comes from an Anonymous source, a 35 year old male from the United States. It features the first threesome we’ve seen in our stories… and a little strip poker action to boot.

If you like reading our First-Time stories, please consider contributing your own story - I need more in order for this series to continue!

The summer after college, I shared an apartment with my best friend and her boyfriend, let’s call them “Janice” and “Chris”. Over the course of the summer, it came out that he was bi, and the three of us had fooled around a little bit, but we’d never done anything beyond oral together.

One night the three of us were hanging out playing poker for chips and drinking cheap beer. Janice busted really fast. We let her buy back in, but just to be dicks, we insisted she take off her shirt. Pretty quickly that devolved into strip poker with losers buying back in for the price of a piece of clothing and a truth or dare from the winners (for the nit-pickers and poker nerds in the audience, we were buying chips back from each other, so the total pool wasn’t growing).

We didn’t get around to the question of what happened to the loser once they were broke and naked until Janice was most of the way there, down to just her panties. We decided that the loser would be “fingercuffs” (this was not long after Chasing Amy had come out. I’m sure the kids call it something different now). I’m pretty sure when I agreed to that, I was assuming Janice was going to be the loser.

After that, my luck turned pretty sour. Chris was definitely the better poker player of us. Janice wasn’t that good, but I’m pretty sure Chris was feeding her chips on the hands where I folded. Eventually, I lost, but not before getting Janice naked too. When I lost my pants, I had to answer the truth, “what has been up your ass?” with “my fingers, my ex-girlfriend’s fingers, and my ex-girlfriend’s vibrator.” When I lost my boxers, they dared me to bend over the back of my chair while they took turns spanking me (with a lot of teasing of my ass and balls in between strokes).

After I lost, it took a minute to dawn on me that we really were going to do fingercuffs with me in the middle. Janice pushed her chair back from the table, scooted her butt forward and hooked her knees over the armrests. It didn’t take a lot of coaxing for me to start going down on her, which put me on all fours with my ass exposed. Chris found a bottle of lube, and started teasing my rear, slowly working around the outside until finally putting a finger in, then a thumb, then two fingers, finding my prostate and massaging it. After what felt like a very long time, he finally pulled out his fingers and I felt the tip of his dick pushing in.

As I mentioned before, I wasn’t a stranger to butt-play then, but that dick felt both larger, and better than anything I had felt before. It wasn’t hard and poky like the vibrator had been, and it varied in diameter. Every time he pulled back, I could feel myself stretching around his head, followed by a thrust and the pressure on my prostate.

After Janice had an orgasm or two, we switched around so that I was on my back, 69ed with Janice as Chris fucked me. Everyone came, things wound down, and eventually we all went to bed.

That night was a couple of weeks before the end of the Summer. Not long after it, I moved out of the state and that was the end of the triangle. It’s been more than ten years since then, and that was my first, only, and probably last encounter with a guy. Now I’m happily married. Sometimes though, my wife will put an njoy steel plug in me while I go down on her. She doesn’t know it, but I like to fantasize that it’s really a guy plowing me while I eat her pussy.