How a game of Monopoly turned into a [MMF] threesome | 2016

This story happened years ago when I was in college and was in a relationship with a girl named Mindy. Mindy and I were pretty serious, I was the first guy she had ever been with and she was my second. However she had an exhibitionist side to her and wasn’t shy. The first time we ever fooled around was in the back of my buddy’s van while he was driving.

You could call Mindy petite. She was 5’4” and weighed around 120 pounds. She had brown hair down to her shoulders. B cup breasts that just blew me away.

One night we were over at my best friend Matt’s house. Matt was a ladies man. Had notches in his bed for every girl he’d had and for someone just out of high school it was an impressive number of notches. He had a slim build, short black hair and stood about 6’0”.

We decided to play Monopoly. An hour or so went by and as things typically go it was getting pretty boring. All the properties on the board were purchased and we were just waiting for someone to go bankrupt. When Mindy landed on one of my properties with a couple of houses, she came up short on funds to pay me. I don’t know what really inspired me, but I had the impulse to say “You can either figure out how to pay me, or you can take off a piece of clothing.” Delighted to see an easy out, Mindy happily took me up on the offer and slipped off one of her socks.

The next time around Mindy’s bad luck struck again and I offered up the same deal. Off came the other sock.

Next it’s my turn and I land on Matt’s Boardwalk property with a hotel. Bummer. He offers up the same deal to me, and off comes my shirt.

You can imagine as we ran short of funds going around the board taking off clothing became the currency of choice. Nobody wanted to lose and it sure seemed to make the game a whole lot more exciting. It didn’t take but 20 minutes between going to jail, paying property taxes, and not passing Go for all three of us to be sitting on the floor in just our underwear.

It was Mindy who came up short the next time. She definitely didn’t have the funds to pay the Park Place tab with a hotel. Mindy looked at me with a look of both disbelief and delight. This game and this night were playing out so quickly that I guess we didn’t realize that slowly undressing means eventually we’ll be naked. I was conflicted about how I felt about this situation. I wanted to see my girlfriend naked, of course, but I didn’t know how this was going to play out with my friend.

Mindy just let out a deep sigh and said “Welp, guess I am going to be the first.” Then reached around, undid her bra, and out came those amazing B cup tits. To say Matt’s face lit up with a smile would be an understatement.

By now there wasn’t any way any of us were actually going exchange any Monopoly money. The game was now just a means to get each other naked. I was next. I landed on Reading Railroad. My property. Dang. Matt was up next. Landed on Mindy’s property, and offered him the deal. Matt stood up, slid down his boxers, and revealed his uncut and half-erect six inch cock.

I was still in disbelief this was all happening. Here is my naked friend, my half naked girlfriend together in the same room, and I have no idea how this is going to end. But based on my rapid heartbeat, racing mind, and ever hardening cock, I knew I wanted this to keep playing out.

Mindy lands on Illinois Avenue, and while she has the money to pay off the rent, she decides it’s better for all involved to just take off the last pair of clothing she has on. She stands up and gently slides down the pair of blue panties she had on down her legs and kicks them off her feet. This is really happening. We’re all getting naked. I’m actually the only one who still has their underwear on. I said “fuck it” and took my underwear off too. Now all three of us are butt naked and we still haven’t finished the game.

Matt landed on one of his properties. Safe for now. It was my turn, and I landed on that dreaded Boardwalk with a hotel belonging to Matt. Matt tilted his head and thought for a minute as he worked out a deal in his mind. Three naked college-aged people in a room lends to some thick sexual energy in the room. We could all feel it. We all wanted something to happen. Without any clothing left to offer up as a deal, Matt looked at me, then looked at Mindy, then back to me and said “Lick her nipples.” I can live with that. I leaned over to Mindy and gave her a soft kiss and to savor the sweet taste of her right nipple for a few seconds. I glanced over at Matt and he was already sporting a hard cock.

Mindy’s turn came next. She went to jail, so she was safe for a round or two. Matt’s turn came up, and landed on Mindy’s property. The tone was set for the rest of the game, so Mindy thought for a second for what he should do. She told him to touch himself for a minute. Matt’s cock was already rock hard, so he reached his hand down and started pumping slowly at first. That is, until Mindy turned around and pointed her petite ass up in the air as inspiration. Matt’s pace picked up a bit, he got a little red in the face, and he very well may have been close to orgasm by the time Mindy told him he could relax.

My turn again and this time I land on Mindy’s property. She orders me to suck her pussy for a minute as she started to lay down on her back. I eagerly get in front of her pussy and start working it like it was my favorite flavor of ice cream. Her pussy is absolutely drenched from the excitement of the previous hour and I see her glance over at Matt while biting her lip to confirm he was watching and enjoying what he saw. I think by this point Matt just had a permanent smile fixed on his face.

At the next turn, Mindy managed to roll doubles and got out of jail to promptly land on one of my properties. “Time to return the favor” I said and told her to give me a blowjob until I told her to stop. After watching Mindy work my cock for a couple of minutes, Matt gestured to me that he wanted to start touching Mindy. I nodded in approval and he grabbed a handful of Mindy’s ass and then worked his hand to start teasing her pussy. As soon as he reached it, Mindy moaned loudly and surged backward against his hand in excitement, as though sweet relief had been granted to her. I told Mindy to stop now, and let’s get back to the game. Mindy was both disappointed and excited and the teasing she had just received.

At my next turn I land on one of Matt’s properties. I could sense a slight hesitation when Matt’s voice cracked and said “I want you to give me a blowjob.”

Wait. What?

When I was younger, I had played naked with some of my guy friends. Touched each other's parts and experimented. I wasn't ashamed of that and was comfortable with myself. But this was for real. I looked at Mindy with kind of a shocked look on my face. She just said “You heard him.”

I said “Come on, man. I’m not like that.” Matt replied “I’m not either but it feels good. It’s just skin, and unless you’re attracted to me, you’re not gay. Give it a try.”

“Ooohhhkkaaaaayy...I mean, just for a second.” Matt leaned back on the floor, and I could see he was nervous. I reached over, grabbed his cock, and stroked it a few times. Then I just decided to get on with it. I slipped his cock into my mouth.

It felt warm, tasted kind of salty, and felt kind of soft. I was definitely no pro, just taking a couple inches initially while I figured out what the hell I was doing. But as a minute or two passed I got the hang of it. I channeled the vision of how Mindy would suck my cock and just applied it to this situation. I was pumping his cock in and out of my mouth. I’d take it out, gently lick the tip and shaft, then go back to putting it in my mouth.

It wasn’t my favorite thing to do at first, but when Matt started moaning and pumping his hips, it started to turn me on big time. I knew I was doing it right and I was starting to enjoy it.

After a couple more minutes I let up and Matt let out a deep sigh. He looked at me and said “Thanks man, not bad!” I just kind of laughed and looked at Mindy to gauge her reaction. She said “Seriously, guys, that was the hottest thing I have ever seen.”

It was Matt’s turn on the game. He rolled, and as luck would have it, he landed on my property. It was only Baltic Avenue, but it was still rent he had to pay.

My curiosity had been peaked. I got past the initial shock of guy-on-guy contact with Matt, and I was definitely interested in more. So I thought for a moment, then told him “You made me do it to you, now it’s your turn. Give me a blowjob” I got up, laid down on the adjacent bed as Matt climbed up and happily put his lips around my cock.

This was a side of Matt I guess I never knew about. He sucked like he knew what he was doing. Worked the balls, worked the shaft, and knew just enough to bring me ever so close to orgasm. I guess a guy knows what a guy wants, right?

Mindy couldn’t take it anymore as she joined me on the bed and started kissing me. I reached down and I could tell just how hot she found this to be. Her pussy was absolutely soaked, and she screamed in pleasure at the first tease of her clit by my fingers.

Matt scoots me further down the bed so I am on the edge, and he is on the floor so he could get a better angle at my cock. Mindy was seated next to me watching it all unfold and enjoying every second.

Matt alternated between licking my balls and sucking my cock for another few minutes before finally leaning back and taking a break. “Dude! What was that?” I said. Matt replied “I would be lying if I said this was my first time with a guy.” I was a little stunned. This was my best friend. I couldn’t believe I was just finding this out, while also confused about what just happened. But I didn’t care. I liked it too much.

Mindy then whispered in my ear “Is it OK if I play with him?” I just looked at the two of them and told her it’s OK, and without wasting a moment Mindy leaped down and started kissing Matt.

While she was kissing Matt I decided I wanted to try out sucking Matt’s cock again. So I got back down on the floor with the two of them and starting going at it. Between Matt’s moaning and Mindy’s squeals of excitement, I knew I made the right move.

Matt then laid down fully on the floor, got relaxed, and told Mindy to “climb on.” Mindy wasted no time by putting her pussy in Matt’s face and letting him get to work. She was facing me while I sucked Matt’s cock. I was enjoying what I was doing.

After a few minutes Matt started bucking in rhythm with my mouth. His moans were getting louder, and finally he backed off Mindy’s pussy to say “I’m gonna cum!” I kept at his cock with the same momentum, and within a few seconds I got the first shot of his cum in my mouth. Then another, then another. Matt moaned and I heard Mindy start to scream as well. I swallowed the first loads and let his cock loose to spray a little more cum onto his belly.

Mindy rolled off Matt’s face and onto the floor, where both her and Matt laid panting on the floor exhausted from the previous several minutes. I just sat there with a smile on my face and a the taste of cum in my mouth.

Mindy looked at me and said “Excellent work, babe!” I replied “Thanks, not bad for my first time I suppose.” Mindy climbed up on the bed, laid down on her back, and told me “I need your cock, right now.”

I wasted no time in climbed up on the bed and sliding my throbbing cock inside of her. Out of the corner of my eye I saw Matt get up and leaving the room to get some water. He re-appeared just laying down beside us in the bed to watch me fuck Mindy. It definitely didn’t take long for me to finish and released a massive load inside her pussy.

In a post-orgasm haze I rolled over still in disbelief over what had just transpired. It was the sexiest thing I had ever experienced but also confused about what just happened with my best friend and wasn’t sure how our friendship would be going forward.

As it turns out, this definitely did not end up as the last experience between the three of us. We had a few more incidents over the next few months, including one with a girl Matt started dating.