The Heist: How I helped my boyfriend fuck a dude in the ass [fmm](long)

This one happened a long time ago (you can probably place the year from some of the references).
I had to reconstruct the dialog, of course, but the events and the plan were all true.
Also, for the sake of a good story, I left out a fair amount of behind-the-scenes discussion and negotiation. Keep in mind, this whole thing happened over a couple of months.

Part 1: The Booty

It was the summer between college and grad school and my boyfriend was dying to fuck a guy in the ass.

Not just any guy, a particular one. Brett was a friend of mine, pretty much my best friend in a weird way. We’d known each other about as long as I’d been dating Josh. Every study group is a mix of people who get shit done, and hangers-on. Brett and I had no tolerance for the latter, so we always sought each other out as lab partners in school.

I totally understood why Brett was the object of Josh’s ass-lust. Brett was tiny, barely an inch or two taller than me (I’m 5’2″) and chiseled. He used to wrestle in high school and still had the body. Every time he moved you could see every muscle writhing and gliding under his skin. Even I wondered what his small, muscular ass would look like bent over.

Most importantly, we both thought Brett was probably game for it. Months earlier, we’d played a particularly raunchy night of Spades combined with “Never Have I Ever” with Brett and his girlfriend at the time. His girlfriend revealed that Brett liked a finger or two during BJs and Brett had admitted to being at least curious about other guys. I saw the way Josh looked when this came up. It took a couple of weeks to get him to admit to it though. It’s amazing what guys will own up to when you have their dick in your mouth.

That was before graduation. Now it was summer. With graduation, the girlfriend had split, our former roommate took a job in Seattle, and Brett took over the last three months of her lease in the second bedroom of our shitty-awesome basement apartment in Central Square.

It was summer after graduation. I’d been working my ass off for 4 years. In a couple of months I’d be working my ass off again for my PhD. This summer, my summer mission was about Brett’s ass. I had a plan, and Josh agreed to it (under BJ duress). Here’s how the heist went down.

Part 2: The Test Run

Before we could reel him in, we needed to get him on the line.

Games were a constant thing that summer. One night the three of us were playing Super Smash Bros, lined up on the couch with me in the middle. After a particularly brutal match where I got my ass handed to me by Jigglypuff, I set down my controller and said, “I have an idea.” I put one hand on each of the boys groins. Brett looked at me a little startled, but I shut that down with a quick, “would you like me to stop?” As the boys played, I stroked them both at the same time. First over their clothes, and then opening their flies when that very quickly got too constraining. After the first game in the match, I announced, “the winner gets a blowjob” as I stroked my hands up and down.

I admit, I may not have created an even playing field, but that was by design. There were a few inopportune moments for Josh where I did a little extra-something, throwing off his timing. Match to Brett.

I slid down off the couch and kneeled in front of Brett, taking him into my mouth and putting my full concentration into giving him the best blowjob of his life. I wanted him to be reckless next time he thought he might get another. Josh stroked himself and watched. After a few minutes, I decided to escalate the situation. I turned to Josh and said, “Now it’s your turn to give the winner his prize.”

I knew he’d never sucked a dick before, and it fascinated me. I’d seen another girl blow Josh one time when we’d had an experimental threesome, but she’d been experienced, without hesitation, and knew all the right things to do. Josh was timid, even tender, and it was sweet. It did the trick. Brett was beyond any objections now, and I sat back and fingered myself as I watched them in their first foray.

Part 3: The Rabbit

We’d broken the first barrier, but there’s still a long way between accepting a blowie and getting fucked in the ass. We needed something that would make Brett charge headlong, heedless of danger. I was going to be the rabbit in front of the greyhound at the track: so enticing, but always just one step ahead. More specifically, my tits were going to be the rabbit. They’re nothing to brag about, but they do come in handy, the leatherman in the toolbox so to speak.

Josh’s thing was Texas Hold’em. He was good. He and Brett had been playing it for years, but Josh was definitely the better player. I came home from a night with my girlfriends, and the two of them were at the table playing practice hands, dissecting the odds. I pulled a beer from the fridge and sat down with them, and we got to playing for chips. I made a few terrible plays (mostly by design), and quickly busted out.

I asked to buy back in again since it was just chips, and on-cue Josh said, “That’ll cost your shirt.” After some token-protest and telling them that they’re dicks, I pulled my shirt over my head and got a new set of chips. A new precedent was set. We needed some rules. Over the progressing hands, we agreed that each buy-in was a piece of clothes. The blind went up one chip each time someone bought in.

I busted out again. Pulling my bra off, the last thing I wanted to be was modest, I saw the way Brett stared at me. I knew I had him. He’d agree to anything.

I asked the table, “what happens if I bust out after I’m naked?”
“Fingercuffs” Josh said (this was back when Kevin Smith movies were a thing).
I pretend-scoffed, but agreed to it. Ok, it’s agreed then. Loser does fingercuffs. And we all drank to that.

Part 4: The House Always Wins

Josh can mop the floor with Brett at poker. Brett knew that too. Brett assumed he could beat me, but he didn’t know that Josh was feeding me chips on the hands where Brett folded. That kept me ahead.

It didn’t take long for both Brett and me to be sitting naked at the table with a huge stack of chips in front of Josh. That’s about the time it started to dawn on Brett that he might actually lose. Of course it was a foregone conclusion.

Part 5: The Payoff

I knew that at this point all I had to do was sit back and play it conservatively. Josh was doing all the work. After what seemed like way too long a string of grindy luck, just barely staying ahead of the blind, Brett finally lost.

I got up from the table, took his hand and led him to the couch. Draping one knee over the armrest, I spread my legs and pulled him down to his knees. Josh had gone to the bedroom to get the lube and condoms. I asked him, “are you sure you want to do this?” and he replied, “I’m not gonna welch on a bet.” I pulled his face down to my pussy, putting him on all fours.

Josh was gentle at first. I could feel Brett’s grunts and moans in my pussy as Josh slid a finger or two inside of him. Every time Brett groaned, I just pulled his face harder to me and reminded him to keep licking. After a long warmup, Josh finally started rubbing his cock against Brett’s asshole. As he slid in, I watched every muscle of Brett’s beautiful back tighten and brace, softening again moments later as he willed himself to relax.

It’s funny, the main thing I remember, the main mental image I took from that was once Josh got a rhythm going, with every thrust, I could see Brett’s shoulders and glutes and back muscles all shifting to brace himself. Over and over again I watched those muscles flex as Josh fucked his virgin ass and Brett ate my soaking pussy.

Source: reddit.com/r/gonewildstories/comments/47nvc5/the_heist_how_i_helped_my_boyfriend_fuck_a_dude