How a game of Monopoly eventually turned into a bi foursome [MMFF] | 2016

This story happened years ago during a summer in college. Here's the first story I had to share.

Over the next couple months following that game of Monopoly, we had a few more experiences between the three of us.

The good news was things didn’t really get awkward. We really didn’t let it change our relationship that much. It just kind of became something else we did. Matt and I sucked each other off a few times. We had another threesome one night that involved Matt cumming on Mindy’s tits.

Eventually Matt started dating this new girl named Jennifer who seemed every bit of a freak that Matt needed. She pretty much wanted sex daily, if not more so. Matt told her about what happened between the three of us and she seemed cool with it, if not intrigued.

Jennifer was a bit more stocky, maybe 5’9” with stringy blonde hair. She had some curves but was overall good looking.

One night we were watching a movie in Matt’s bedroom. Mindy and I were sitting on the floor. Matt and Jennifer were sitting on the bed. About halfway through the movie I glanced up at them and I could tell they were getting handsy. About 10 minutes later I look up and see Jennifer sitting up completely topless. Jennifer had huge tits. I don’t claim to be an expert on large cup sizes, but there was plenty to work with.

I took that as my cue for the evening’s plans. I tapped Mindy on the shoulder and pointed towards the bed. Mindy just turned back to me with a slight smile on her face and said “Oh, alright then!” and just chuckled. We started making out, and over the course of the next several minutes Mindy and I’s clothes started to come off.

Jennifer and Matt stopped long enough for Jennifer to notice our heavy petting and the removal of clothes. Jennifer slid down beside us with a smile on her face. Matt just looked on.

“Iiiiiiiiiii have a question for you Mindy.” Jennifer said. “What’s that?” Mindy replied. “Have you ever kissed a girl before?” I think Mindy’s face turned a fairly dark shade of red.

Mindy stammered “Uh...n..n....noooo....".

"Do you want to try it?" Jennifer replied.

Mindy just stared at Jennifer for a minute, and mustered a response of "Uh...I mean...uh...ye.......yeah.......I guess."

And within a fraction of a second, Jennifer had her face planted on Mindy's.

As the moments went on tongues start to slip in between their mouths and I could tell the more Mindy relaxed, the more she was into it. Her breathing got deeper and as Jennifer would start kissing her neck even let out a few "Mmmmms" in approval.

Pretty soon Jennifer’s hands were feeling up Mindy’s body. They took hold of Mindy’s B-cup tits and she gently massaged them. Her hands started working lower, and upon reaching Mindy’s panties Jennifer said “I don’t think we’ll be needing these anymore.”

It’s like the reveal of Mindy’s beautiful pussy happened in slow motion to display her trimmed bush in a landing strip.

The two girls went back to kissing and Jennifer’s hand started to gently rub on Mindy’s clit. Mindy closed her eyes and leaned back a bit to just enjoy the attention.

Matt and I were definitely enjoying this show. Both of us sat on the edge of the bed and I reached out and started stroking his cock. He reached over and intertwined his arm and returned the favor.

Matt eventually let go of my cock, rolled onto his stomach, and took me into his mouth while I sat up to enjoy the show of the girls playing with each other. By now both girls were totally naked and Jennifer’s freshly shaven pussy was on display. They were both lying next to each other making out and Jennifer had her leg wrapped around Mindy’s and was grinding her.

“What a life” I thought. Watching two naked girls go at it while my dick gets sucked.

After a few minutes Matt sits back up next to me and he looks a little nervous. Kind of like the first time he asked me to give him a blowjob.

“So, the girls are obviously busy. Anything you want to do?” He asked. “Oh I dunno, I was certainly enjoying myself there haha.” I said.

"Heh, yeah, that view is pretty awesome. Jenny is definitely bi so that’s nice” He replied.

“Well then that works out for everyone. Mindy seems pleased.” I said.

By now Jennifer had made her way down to Mindy’s pussy and began licking every part of it. Mindy just kept her eyes closed and worked her pelvis against Jennifer’s face in rhythm.

“Hey, ah, I was kind of thinking about trying something.” Matt said.

“What’s that?”

Matt said “I was kind of thinking I might want to try having you fuck me…….but...we don’t have to if you don’t want to.”

I had never tried anal before. Much less with another guy. I just thought about it for a couple of moments and realized I didn’t really have a good reason to say no. I had experimented quite a bit already and enjoyed myself so this was just another item to check off the list.

“I guess we could try it. Do you know what to do?” I said. “I’ve played with some toys, so I think I can handle it. Just go slow” Matt said as he reached over to a box below the bed and pulled out a bottle of lube.

At some point I heard Mindy have what must have been the best ogasm of her life. My mind was racing on the opportunity in front of me so I wasn’t really aware of what else was happening in the room.

I grabbed a handful of lube and Matt laid on his back, put his feet in the air, and waited for me to enter him. I had to admit the sensations and the positioning didn't feel much different than a woman. I reached down, felt his hole, aimed my cock, and slowly started working my way into him. Just trying to “get through the door” was a chore in itself. I gently pushed my cock and could feel it start to enter, worried the whole time about how it was feeling for him. I could tell he was uncomfortable as he had a pained look on his face for a few moments or so. But he reassured me it was OK and to just keep at it.

I think I was entering him mere centimeters at a time. His hole felt like a clamp. It was incredibly tight. Matt would take deep breaths and each time I was able to get a little bit more inside him.

“This looks like fun” Jennifer joked. At this point the girls were wrapping up whatever it was they were doing. I was so caught up in in the nerves and anticipation of the situation I had almost forgotten they were there. Matt gave out a breathy reply of “I’ll let you know in a minute.”

The girls just laid out on the bed on their stomachs to watch what Matt and I were doing.

What felt like an hour later, I looked down and noticed my cock was just about entirely inside of him. I asked Matt how he was feeling and he would just nod in approval.

At this point I finally tried to take my first real thrust. I pulled back and when the head of my cock was just about out, I slowly pushed back inside. Matt winced, but took another deep breath and relaxed some more. I repeated the thrusts a few more times and heard Mindy whisper something to Jennifer and they both giggled. After a few more thrusts, it started to get easier. After a minute, Matt let out a moan and a “OK, this is starting to feel good.”

Jennifer moved over a couple of feet and kissed Matt. Then turned around and kissed me. I guess this is what being in a porno feels like? It was pretty surreal.

Matt asked to shift positions. He wanted me to fuck him from behind. He put his legs on the floor and laid his stomach out on the bed. I approached him from behind and slid my cock back into his ass. Now that he was relaxed I was able to enter him with little effort. I pumped at his ass for another few minutes or so while the girls just looked on. I could tell they were both very much enjoying the scene as I could see their hips grinding on the bed now and then.

This definitely felt different than fucking Mindy. It was really tight and not as wet as a vagina but it felt good. Matt was pushing back on me and grinding against me as I thrusted. We had a good rhythm that made it feel like good sex.

Matt pulled back out, laid on the edge of the bed and let me enter him missionary again. He said “Please make me cum.” I was very happy to oblige, as I fucked him again for another couple of minutes while he stroked his cock. When Matt came I could feel the pulses on my cock while his load shot probably 10 feet across the room. He screamed in delight.

“That….was….incredible.” Jennifer said.

At this point I took a break to head to the bathroom to clean up and get some water. Mindy followed me into the bathroom and asked how I felt. “That was...different...it was…..interesting” was all I could answer in between breaths. “Well that was interesting to watch. Looks like you enjoyed yourself” she replied.

“How about you? How are YOU doing?” I asked. “Oohhhhhhh mmmyyyy gooooooooooood. I love you honey, but Jennifer’s tongue does things I never even dreamed of. I had one of the best orgasms ever!” she told me excitedly.

“Heh, that’s what it sounded like to me” I said.

I came back into the room and laid out on the bed. My rock hard cock had softened a bit, and Jennifer had taken notice.

“Can I have a turn at him now?” She asked Matt. “He’s all yours.” Matt said. Mindy just nodded in approval at the situation.

Jennifer wasted no time and taking after my cock. She could take pretty much my entire 7 inches down her throat. Nobody had ever done that to me before.

Soon she sat up, straddled my legs, and slipped my cock into her incredibly wet pussy. Jennifer just bucked and moaned for a few minutes then shivered with an orgasm. As she cooled down she turned around to tell Mindy “You’re up!”

Mindy took her cue. Much like Jennifer, she straddled my legs and inserted my cock into her also incredibly wet pussy. It was occurring to me that my cock had had now penetrated three different people in under an hour. I just smiled as Mindy continued to ride me until I started building an orgasm. The fury of all that buildup with so many people seemed unleash in load after load into Mindy’s welcoming pussy.

She climbed off, rolled over on the bed, and we all laid in a pile of naked bodies. We chatted for a bit about the amazement of what just happened and just kind of pet each other’s bodies.

We all got cleaned up and said our goodnights since both Mindy and I had to work in the morning. That was pretty much the end of our sexual exploits as a couple of weeks later Mindy and I went back to college and Matt was eventually deployed in the Army reserves. We’ve fallen out of touch since then (and Mindy and I eventually broke up) but I still think about that amazing summer we had together.