My first threeway with my roommate and his girl friend. [M/F/M] | 2016

Background: My roommate is kind of a douche. My other two roommates don't like him much. He can be kinda cool but more times than not he likes to think he's better than us. His girlfriend is also the same. They're great together. However, his girlfriend, Cassi, is smoking hot. She' 5-foot-8 inches, size b-cup bra and an ass that you wouldn't mind suffocating in. She's got normal brunette hair past her shoulders and crystal white teeth. She's an absolute freak and loves flashing our group of friends when she gets drunk and even gets handsy with all of us at times. Their relationship is pretty weird because he doesn't really care. That's how I had my first threeway.

A couple years before this happened, the three of us were sitting around joking about who the best three way options would be in our friend group. We came across the topic of the three of us doing it and it was kind of a running joke at the time that we'd do it sometime before we left college. Fastforward two years and you get the night of our threeway.

Her and I had been flirting all night. I grabber her ass a few times in these slick fitting yoga pants. I told her I wouldn't mind if she sat on my face and she said she wouldn't mind either. At one point, however, she and I were playing beer pong and she slid her hand down the back of my shorts and started fingering around with my gooch area. Slightly aroused, I started doing the same on the outside of her yoga pants. I could feel her getting wet. She wasn't wearing any panties; it was so nice.

She leaned over and asked if I'd be down with a threeway if her boyfriend, Travis, didn't mind. Horny as shit I said yes because there was no way I was going to turn down that ass. Alarmingly enough, he came up to me and said "so I hear you want to fuck Cassy." I said " sure do. I'd be dumb to turn that down because you know she asked me. So it'll probably happen whether you want it to or not." He laughed and said alright and it was on from there.

Once people left our apartment and jumped into his room across the hall. She was just sitting at the foot of his bed, in her bra and nothing else. She gave me a wink and said, "I hope you're looking forward to this as much as I'm looking forward to having your cock in my ass." She really didn't wait long to shut off the tv and and unbuckled my jeans. Travis just said there, watching and I assume enjoying this. She threw down my pants as I took off my shirt. I was already hard-ish from her just being so close to my dick. Then, with one sweeping motion of her tongue from the base of my five-inch cock, she stuffed it straight into her mouth.

I grabbed the back of her head with both hands and started to choke her with my dick a few times. The Travis said "why don't you come over her so I can have some fun with your ass, Cassy?" So we jumped on the bed, me at the head of the bed on my back, her blowing me on her stomach, and Travis at the foot of the bed eating out her ass.

"Shit, Cassy, your fucking wetter than the ocean down her," Travis said as he popped up after about three minutes of pussy eating.

"Well having your tongue in my ass and Chris's cock in my throat makes me horny as shit. You guys ready to fuck?" Cassy said.

So without hesitation, Travis whips out his dick and starts smashing her ass doggy style. She's moaning laying with her face in my balls, just holding on for dear life to my cock. That's when Travis said "don't just sit there, stuff your dick in her mouth!" So I did and it muffled her moans. After about five or ten minutes, we switch.

This was by far the best part. I stuck my dick in her ass and watched as she backed up into me. It was the best doggy style sex I've ever had. Travis and I ended up Eiffel Towering her. She looked back over her shoulder and with what breath she had, she told me to " stick it in my asshole while Travis fucks my soaking pussy."

I stopped, looked at Travis and he said "she's the boss. In what was the best sexual moment of my life, Travis laid down on his back at the end of the bed. Cassy got on top in the riding position, and I got behind her and put my dick in her tight little asshole. It was so tight I thought it was going to get stuck! Luckily, we were home alone because she was screaming and screaming. At some point, Travis came in side her and she just kept riding. When I couldn't take it anymore, I pulled out, grabbed her waist, pulled her off of Travis and threw her on her back. I straddled her little titties and popped a couple shots of cum right in her face and in her mouth.

For about 20 minutes after we all just laid there, naked and covered with sweat and cum. She said "we tell no one of this. Ever." We all agreed, until now. If you count this as "telling someone." Although it was another guy and girl, it was the hottest and best sex of my life.

TL;DR - I got to fuck my asshole roommate's hot girlfriend, I got to have a threeway and I popped her in the eye with my cum. Successful fuck.