This happened around 3 years ago. To start, let me explain the situation with this girl. We're in our late 20's and I met her through a social circle I have through work. I work in a field that is surrounded with upper class people, luckily I did well in school and landed myself a "sexy" job. With this comes friends that have great money and being around incredibly attractive women all the time. I myself am a pretty attractive guy, probably in the 7-8 range, however in the size department and in bed I always have struggled. I've been working on my confidence in that area and have improved but it's always in the back of my mind when hooking up with girls. Because of this and prior experiences, I have developed a submissive side to me when it comes to sex, which will play out later on.

Anyway, I met this one girl, we can call her Rachel. Her and I really connected well after meeting at a bar for drinks with some people for work. Rachel is your picture-perfect, gorgeous old money styled brunette. One of the most stunning women I've met in person. I was surprised by her interest in me and we exchanged numbers. Long story short we ended up texting a lot and I asked her out to drinks. She is way out of my league so I wasn't getting my hopes up, and then eventually to my surprise we hooked up.

I really gave it my all with her, and I think I did a decent job, she was great in bed and not a starfish like some of these high end girls could be. After we fucked a couple times I was honest to her about my insecurities and submissive fantasies. I asked her to be honest about how I was in bed, what I could work on and whatnot. She was very honest and said I was ok, gave me some pointers and what she would prefer in a general sense. It honestly turned me on so much to get in her mind to figure out what turns her on. More and more she was honest, and she started to get a kick out of me being the curious boy I was. She told me what size she prefers (larger than me), body type (a nicely toned man, but not too muscular), tall, and most of all she just wanted the man to be dominant in bed and carry that confidence into personal interactions as well. It was all so hot to hear for the submissive guy I was becoming, realizing that I can't really match up to all those things.

After these few conversations, she saw me more as a friend and we stopped fucking, whcih was a shame, but makes sense and I couldn't complain, I banged this smokeshow that most guys couldn't dream of it. Anyway a few months went by and she ended up in a relationship with some guy. This man definitely was more of her type, like a Greek God. We didn't talk as much during this time till one day she texted me out of the blue.

She asked how I was doing and had typical catching up small talk. Eventually she told me about her new man and then this is when it all clicked in my head. While I got off to the fact she was honest about the kind of man she wanted, I think she got an even bigger kick out of teasing me with this whole idea. She started talking him up, saying how great he is and what not and I just knew she was grinning on the other side of this conversation, gloating about him to me. I kept asking her more questions about him, about his looks and what she likes about him (his body), his dominant personality, etc. It was so hard hearing her talk about him. I told her I was happy she finally found the man she needs. Then she hit me with a "Yeah, I'm sure you'll get a kick out of imagining me with him".

I was so turned on when she told me that. All I said in response was "You know me too well". She didn't respond, and I didn't hear from her for a little while, but you bet I was jerking off imagining that man plowing her. I really started to realize how submissive and how much of a voyeur I was.

A couple months went by again and I hadn't heard from her, she never posted about him so I assumed they were just fucking and not that serious, or keeping it on the downlow. Then again, I received a text out of the blue from her...

"Josh and I have talked about wanting to do a threesome with another guy, I figured I'd invite you in since I'm comfortable with you and I know you won't make Josh feel insecure".... What a hot fucking way to ask. I was stunned and thrilled. I obviously said yes and asked how we should set this up. I was so excited to see this man rock her world and also get another chance at that pussy. It felt surreal like I was living a fantasy.

So we set up the plans to meet. We first all grabbed drinks together to get comfortable so that he and I can see that it won't be weird. In person it was even more obvious, the guy was quite tall and had an aura of just confidence. He was a great dude, super easy to talk to, which made me more comfortable. We talked very generally about what was gonna go down and planned a date at a hotel, reserved the nicest suite we could, and that was that, it was set.

I'll skip to the night of since I have been rambling on...

So we all arrived at the hotel. They were already there when I arrived, I got to the room and knocked and Rachel answered looking absolutely amazing. Wearing a black lace lingerie set I almost came in my pants when she answered the door, she immediately gave me a kiss on the lips and led me over to the bed where Josh was. She started making out with both of us, both of us surrounding her and feeling her up as we kissed. Then she slowly got onto her knees…

I’m about average size, but when she pulled down Josh's jeans and saw her reaction, I almost had a similar reaction lol, the man was PACKING

She started off by giving me a blowjob whilst Josh went down on her. She came pretty quickly but that is normal for her from getting head from when we used to fuck around. Then we swapped and I started fucking her from behind as she gave Josh head. I could tell she was so horny sucking on Josh's cock that she barely noticed me inside of her. We swapped again and this time Josh started fucking her and it was a whole different experience. He was hitting places she didn't know existed inside of her . After a while she had to stop sucking me off as she was about to cum, she never came from sex with me so this was a first for me to see. She was extremely loud at this point as she built up to orgasm. Finally, she came hard, but not only that, she was shaking and was moaning his name so loud, she couldn't control it. My mind was melting from the sexual imagery (practically art) I was seeing as I was left to pretty much take care of myself while I watched. Seeing these two incredibly hot people fuck was amazing, she looked sexier than ever with her running her hands all over his fit body when she straddled him for more.

At this point I didn’t even care that I wasn't involved. It was fucking hot to see her in this state. I just jerked off as she rode him and hearing them fuck and moan into each other's mouths, seeing that thick cock of his stretch her out and glisten from her pussy wetness. Shortly after he started to tense up, moan loudly and he unloaded in her, it was so hot to see his dick throb inside her as they both moaned. At this point I had to cum, and shot pretty much at the same time making a mess of myself.

They collapsed on the bed and I sat there just mind blown at what I had witnessed. She came over to me to kiss me and told me "Now that's what good sex looks like"... God this killed me, but turned me on in ways I couldn't imagine. Josh himself said he's never seen her so crazy, and it was clear that she was turned on to prove a point to me, that she basically brought me in to "cuck" me after what I told her about my submissive fantasies, that she came so hard teasing me and making me watch.

It may not be the healthiest sexual experience but honestly it was so fucking hot, I relive it all the time and I can't thank her enough, it truly was my biggest fantasy lived out