My boss called me an escort as a present for my birthday and watched us have sex [M]28

Never posted here but recently discovered this subreddit and I have got to say I have been enjoying all the stories shared. Not many stories from guys but hey, I need to tell this to someone and I definitely can’t tell anyone I know personally so here we are.

This happened to me few months ago for my birthday.

I was assisting my boss [M65] with some work few days before my birthday, I love my boss and we are now more friends than colleagues as we have worked together for 5+ years. He’s an older dude that loves to have fun while working (who doesn’t?).

This day was special as one of his old friends came into the studio for a commission. I had met the guy only once maybe 2-3 years ago so I remembered his name but he barely remembered my face. By lunch time we were already down few bottles of wine (a constant on our workdays) and not slowing down at all, in fact we got all the work done by mid afternoon. Needless to say by the evening we were pretty drunk.

Not sure how it all started but by the end when I was finishing tidying up the two older guys where just watching porn and talking about old days stories with girls and general comradery. Turns out from the stories that my boss has a very big fetish about voyeurism and watching people fuck in general. Pretty sure the other friend [M50+ I think] was Bisexual and I could feel him hinting at me a bit in a somewhat flirty way. My Boss confirmed this but I made it very clear that I had no problem with people being Bi or general advances but I am definitely 100% straight so he was not gonna get any luck with me. This said I quickly joined in with my very limited stories (I have been with the same girlfriend for many years by now and absolutely never cheated on her) but I do enjoy porn as every guy on the planet so why not.

After a while the old friend has to leave to get home and, reluctantly says goodbye while wobbling out of the door. Meanwhile my boss keeps fantasising on how in the old days they would have called in a couple of escorts and keep going till the morning. Then suddenly he turns around to me and just whispers:” Shall we?! It’s your birthday after all, my treat!” It takes me a second to realise what he means and I quickly give in. Original plan was to call one escort in for me while he would just watch us fuck while jerking off on the side (we had already cleared that I wouldn’t have minded him being on the side watching), but on the phone they would have not send 1 girl to 2 guys so we ended up calling in 2 girls.

While waiting my boss starts asking me if I would ever consider letting him watch me and my girlfriend having sex (they have met before and she is pretty damn hot as well). I reply that I might consider it but I doubt she would as I don’t think she would like the idea. He even enquire if he could watch me while his wife (yes this guy has a very nice wife that I have met few times) [F50 and very good looking] gives me a blowjob; again I reply that I would need to think about this.

Quick shower to freshen up (very much till stunk of booze probably) and the girls arrive. In the meantime I went to the ATM with by boss card and got cash out for everyone.

My boss keeps mentioning to the girls that he doesn’t really want to do any action so the ladies should just focus on me but they are quite clear that they will only do 1 on 1. I am a bit disappointed as a threesome its one of my biggest fantasy and this time it got so so close!! And it would have been with 2 absolute babes. We all four go to my boss bedroom and I settle in with Katie and he gets Vicky.

I am super nervous and clearly never done anything like this before so I tell Katie to take the lead and she is great. Petite dark hair with an amazing ass and real perky boobs. First she undress me and then sits me on the bed before getting on her knees and start jerking me off and then blowing me. She even had a tongue piercing which I always wandered how it would have felt, turns out I am not 100% sure I like it, in general just a little underwhelming but would definitely try again.

I am in heaven, drunk, with a hot girls sucking my dick and with my head I can see blonde Vicky giving a naked lap dance to my boss which he’s watching us all. We only have 1h so I make it count and as soon as I my nervs relax I start fucking Katie in every possible position properly pounding her especially doggy style. That ass is just incredible. My boss watches every move while grabbing a bit of Vicky and giving her some gentle spanks but, as he mentioned, no more than that. After around 40 min I am done and I am even surprised I lasted that long to be honest. Girls leave and I am still shaking for the excitement. I thank my boss for the birthday present, he compliments my dick, and go home still shaking by the amazing experience I just had. (I know for some people this sounds very normal and not very “extreme” at all but as I mentioned I have been with my girlfriend for many years so my sex life has been pretty limited in that sense.)

Got to say I have spent the following 2 days looking up other escorts and fantasising about doing it again… wondering if I’ll have to wait another year for my next birthday present or if this time I should just treat myself… and who knows, maybe there will be more stories to come with my Boss.

Source: reddit.com/r/gonewildstories/comments/kzspwp/my_boss_called_me_an_escort_as_a_present_for_my