What. A. Night. | 2016

This happened a few years ago with my ex and her new bf I mentioned in this thread.

Met up with the ex and her bf with my "new" gf of 8 months at the time. The gf knew we had a MFM threesome in the past, but she's not interested in women at all. I mentioned I'm comfortable with us trying out an open relationship if she was interested, so long as I'm there to manage and set boundaries. She agreed and we met up for drinks.

We went back to his place, had some shots to loosen up, and my ex and her bf started going at it so my gf and I started getting into it. My ex and him took a break and she came over and gave me head while I went down on my gf. When he came back in we all moved from the couch to the bed and I went down on my gf some more. My gf broke ground too and she actually pulled my ex over her and gave her oral which was pretty hot and I was totally cool with. It was when he pulled out his condom where I froze and my nerves kinda went. My ex tried to reassure me and make me comfortable, but I still balked and just wasn't comfortable in that moment seeing him about to enter my gf.

We backed off a bit and my gf and I talked as she rode me over on the couch while my ex and her bf did 69 and he fucked her missionary. We went over to watch and she just got up close and personal with his dick. I was curiously excited I guess and I told her to go down on him and give it a try, stroke him a bit, and touch it so I could get used to the idea. She held it up to her face which realy just accentuated his rediculous size. It was one of those "you had to be there" moments.

I have no idea why, but that and my gf and ex making the point that 'we've all be with other people before and we're okay with our respective SO's so this is no different' supercharged my comfort. My gf put the condom on him, we all got on the bed and she started to give me oral again, my ex on the side playing with my gf's boobs. This way I could see everything and felt in control having my hand there in the middle of it rubbign her clit as my ex guided him into her. This part was actually comical because she couldn't take him and we tried and tried, but she was too tight. I went back to fucking her some more to take her mind off it. He sat there next to me with my ex going down on him, and when my gf was coming I moved out of the way and he took over my spot. When she was relaxed and recovered him tried to enter her. This time there was a "pop!" followed by a biiiiiiig moan, her legs shuddering, and her eyes rolled in the back of her head while he SLOWLY thrusted inside her. He could fit maybe half-way inside, but it was still hot as fuck. And I shit you not, he got maybe 4 or 5 long slow strokes and she had the most powerful orgasm of her life*. We moved off the bed and bent her over and I did her doggy style with him standing next to me while my ex went down on him some more. I pulled out, he spread her cheeks a bit, and in he went. I moved to the front so she could give me oral some more, and my ex went underneath and sucked her clit. Bam! Another huge orgasm. From this point I banged my ex 6 ways to Sunday and he started really getting into it once she relaxed some more and got more comfortable with his girth.

We took a short break and I went back to my gf and my ex went back to him. Gf whispered "thank you" a bunch of times and things to that effect and said to give it to her from behind. Gf was noticeably looser, but fuck it. I thought she meant doggy again since she NEVER wanted anal before and was adamantly opposed. If I even got too close before she'd freak. We started with doggy, but she moved my hand and inserted my thumb into her booty and that's when it clicked. I lubed up and in it went. We both got to watch my ex on top of him though and were equally amazed when she took him to all the way in. both on top and doggy at one point. He even gave us a porn shot where he moves to the side and spread her ass cheeks a bit so we had a visible angle. Wild stuff.

Awesome night overall and I really got past a lot of hangups I had with a woman I was dating being with another guy, so long as I'm there in control and comfortable with what all is going on. And final note, I was about to cum in her ass and she spun around and effectively deepthroated me and I blew a huge load straight down her throat, which is something I'd never done in my life up to that point as far as I can remember. Verdict: Best. Sex. Ever.

*She looked at me and almost cried when we talked about it later because she felt so guilty orgasiming so hard with him and not me. We talked it out and smoothed things over and reassured each other it was fine.