I fucked an Instagram escort in front of her boyfriend [MF]

Sexually speaking, I’m not that adventurous of a guy. Sure I like some stuff, and I watch porn, but I wouldn’t consider myself super kinky. ​I usually take the woman’s lead and just go with the flow.

For the last year or so, I’ve been hiring escorts. I found this online Madam that was pimping out Instagram models. At first, I was a cynical skeptic on this, but it worked out and we’re all happy with the arrangement. One of the models that I hire on a regular basis, Allison, she’s cool, laid back, chill. She also has a boyfriend who knows about her ‘side job’. All good in my opinion, the last thing I want is drama. We’re all adults here. And there is a mutual understand not to mess with a good thing.

One night, after one of my paid bookings with Allison, she’s cleaning up and getting dressed. That’s when she approached me and asked if I’d be interested in getting together again. Yes, of course. I feel super comfortable with her. But that’s when she drops this kinky bomb on me. She is wanting to get together, but have her boyfriend there. A threesome? No… just him watching. Again, I’m not super kinky, and I’m somewhat private. So a request like this is a bit unusual and out there for me. She can probably tell that I was surprised, so she said that it’s something they do as a couple. Something that they both enjoy and it’s one of their things.

At first, I was going to politely decline. More power to them, but again I just don’t want any drama. But she seals the deal and closes me, by saying that it would be free, no charge. A thank you for indulging in their private kink. So that convinces me, and we set up a date.

When we all got together, we met at the hotel bar. I was fucking nervous. I haven’t really ‘performed’ in front of anybody, especially like this. This isn’t really my thing. The boyfriend was actually a pretty cool guy. Fucking ripped – he’s a personal trainer or something. Someone you wouldn’t really expect to enjoy sharing his gf. Allison and the bf seem really cool and chill, and they got me relaxed enough to head upstairs to the room.

Upstairs, Allison and I did our thing. I felt like I needed to ‘perform’ or act out a ‘performance’. But honestly… I forgot all that once we got into all the sexual stuff. The boyfriend was just seated off to the side. Drinking a beer, enjoying the views I suppose. He didn’t whip out his dick or make a move on me (we discussed ground rules beforehand). It was surreal in many ways. 1: I’m fucking this hot Instagram model, 2: it’s for free, 3: and it’s front of her personal trainer boyfriend. During the fucking, we did cater to his views. Like the angels, the positions. And she did play it up. She was talking to her boyfriend. Not in a demeaning, cuckold type of way. But in a ‘look how hot this is, and he’s so fucking big’ (such an ego trip for me if I’m being honest). She did this while in doggystyle, while we were facing him. The boyfriend wasn’t really directive or tell us what to do. He was just watching, listening…

For me, this is all hot and crazy. Never in a million years would I think about even trying something like this. But since Allison brought it up, it was kinky as fuck. Towards the end, I was just going fucking crazy. Pounding and railing her as much as possible, which she thoroughly enjoyed and played up. Eventually I came all over her boobs (by her request). That mixed with the sweat and stuff, she was a hot mess at the end.

I would have thought this would have been this most awkward part. Allison and I are done, and I didn’t know what to say or do next. In a way to break the awkward silence (for what seems like a long time, but in reality it was probably only a few seconds), I just blurted out ‘Was that what you guys were looking for?’ That’s when the boyfriend got up, approached me… and just gave me a fist bump. ‘Yeah dude, fucking awesome!, thanks!’ Whoa, weird but that’s when I realized that different people are into different things. I’m into paying for instagram escorts, others are into swinging, others are into watching. Whatever floats your boat – we’re all consenting adults. I wouldn’t exactly say that I completely understand everything, but after that, I get it.

After we got dressed, we actually went back to the hotel bar and got a drink. After a beer, I felt like the third wheel, and just wanted to give them some privacy for boyfriend/girlfriend stuff, which they were cool with. As I was about to leave, she reaches out and thanks me, and asks if I would be interested in doing something like that, or more, another time.

Source: reddit.com/r/gonewildstories/comments/civtoh/i_fucked_an_instagram_escort_in_front_of_her