I accidently turned an IG Model into an Escort [MF]

I’m at the age where all my friends are getting engaged and married.  Hey, happy for them.  But as a single guy, it kind of stinks when you go to the wedding, stag.  And when you are constantly being asked, hey when are you going to settle down?  I’m sure I’ll do so eventually, but just focusing on my career and honestly… I’m having tons of fun being single.

There was one wedding, where I honestly just didn’t feel like going single. Plus weddings are more fun when you have a date to hang and dance with.   Normally I’d ask one of my platonic female friends, but the schedules didn’t line up.  So one random night, I was on IG, and I just said to myself, why the fuck not.  Let me ask one of these models if they would be interested in being my wedding date.  So I shot my shot.  Nothing to lose here.  So I DMed one (let’s call her Kate) that I’d been following, and introduced myself and just asked.  I wasn’t looking to hook up or do any creepy funny business with.  Very professionally sounding – just looking for a +1 for a wedding.    

Surprisingly enough, Kate responded and we got into some dialog.  It was probably the fact that the wedding was in a cool location, and I offered to pay for her travels.  I sent her all my info, name, cell, work website, linked profile, etc.. Just to show that I’m not some random creepo.  And I offered to pay her for her time.  Just like a modeling gig.  If she’d be my wedding date, I’d pay her, we would enjoy the wedding, and after it wrapped, we would part ways. Again, no funny business here.  It was clear that she was hesitant – so we met up at a coffee place, she brought a friend with her.  And we just chatted in person for a few.  And yeah, after some back and forth on expectations, etc… Kate agreed.  

The wedding itself was great, as most weddings are.  Kate was fantastic.  Played the part perfectly.  First off, she is drop dead gorgeous.  And the fact that she was my arm/eye candy, wearing a sexy dress basically wow’ed everybody.  She knew her ‘role’ and just played it up.  Complete ego trip for me, as my buddies were jealous.  Honestly, it was really cool to actually have a model as a wedding date, to hang and party and dance with.  On that first date, I’m sure most of it was acting, but hey we both know what the deal was.  After the wedding wrapped, I paid Kate for her time, and just parted ways.  Super chill on both sides, and yeah it was as easy as that.

It just so happened that I had a bunch of weddings to attend, at the same time.  So I texted Kate if she’d be interested in another ‘gig’ and yeah she was.  So it was rinse and repeat.  There was less ‘are you some weird creep’ phase, and more of the fun wedding stuff phase.  So yeah, Kate agreed.  I’d buy her something to wear.  We would hang out and party at the wedding.  And I pay her afterwards, and we parted ways.  Super chill.  And during all this time, there was some chemistry brewing.  Not love or anything, just some mutual attraction.  I’m sure the partying, the glamour of the weddings, the alcohol – didn’t hurt.  But yeah, there was some flirting and attraction.  

After the 4th wedding or so, we were very comfortable with one another.  Dancing, flirting, grinding.  At the end of the night, that’s when we would normally pay her and part ways.  I shot my shot again.  “Hey, do you want to come upstairs and have a drink?”  “Sure, I’d love to”.  So yeah, Kate came upstairs to my hotel room and we hit it off again.  That wedding chemistry translated over into the bedroom, and we just went at it.  Pure lust.  Fucking.  It was incredible.  Obviously, she has the most perfect body.  And I’m no slouch myself.  But yeah, easily the hottest woman I’ve slept with and the best sex I’ve ever had.  I don’t normally do this, but at her insistence, I finished all over her face, which was glorious.  Then I finished her off afterwards, and she just squirted all over the bed.

So after all the fucking, we cleaned ourselves up.  And here’s the thing.  I paid her for her time, and we parted ways.  I didn’t really think much about it until a while later.  Wait a minute.  What did I just pay for?  The wedding, or the sex?  Or…?  Fuck, I didn’t want her to think that I’m some weird creepy John or anything.  Fuck, didn’t want to screw up a good thing here.  

So I called Kate the next day, to clear the air.  Hey, are you good?  Didn’t mean to imply or suggest or offend….. No, she’s good.  She had a great time.  Don’t over think this – is basically what she said to me.  So if she’s good, then I’m good.  

The next +1 need that I had wasn’t a wedding – actually a work trip.  So again asked Kate.  “Hey, want to come with me to the work trip?  It’s an overnight… and I can get you a separate room”.  “Sure, would love to join, and one room is fine”.  Something like that.  And yeah, there you go.  So fast forward, we’re at this work dinner.  Wives and girlfriends included.  And Kate comes strutting out with me.  Complete bombshell outfit.  Like with weddings, you dress up elegantly and such.  But this work thing – all people around our age, little bit more casual, party like.  She wore this bombshell, leave nothing to the imagination type of dress.  Wow, simply wow.  Pretty sure everybody’s jaws dropped.  
Anyways, we’re hanging, drinking, all that stuff.  And like last time, we head back up to the hotel room.  She brought some lingerie this time (and an overnight bag), and changed.  And we fucked like animials.  And like last time, when the trip was over, I paid her and we parted ways.  The next day, my work colleagues were all curious about her and us.  Needless to say there was some envy.  Again, with me and Kate – don’t over think this, we’re all good here.

So this continues for a while.  Sometimes its a wedding.  Sometimes a work thing.  Sometimes it was just a weekend getaway.  Maybe Kate wore an elegant gown to one, to a sultry cocktail dress to another.  Or even this one work thing, where I was on stage.  She came out with me, basically looking like a high end escort (at her insistence).  More tits and ass and high heels than anything.  It was great.  She’s a lot more kinkier than me.  And each time, fucked, payment and parted ways.  It never grew much past that.  Sure she met my friends.  And I met some of hers.  But it’s not like we spent the holidays with one another.  Or that there was actual love.  

Sometimes someone would recognize her.  She didn’t hide that fact.  If we were asked how we got together – a mutual friend played match maker.  If one of my buddies asked about our sex lives, then I’d pull up some random lingerie pics of her on my phone.  (no x-rated content – one of her rules, which is completely fine).  

Eventually this fling between Kate and I fizzled out.  The pandemic hit, and we ran out of ‘events’ to get together on.  When it was safe, we did meet up and fucked (for free) a few more times, but the chemistry eventually fizzled out.  We do keep in touch from time to time.  In fact I recently ran into her, by sheer coincidence.  Kind of had our little own exit interview.  Turns out, that I was the only guy that she did anything like this with.  And she actually dated a few guys, while she was fucking me.  Some knew she was escorting (her words), some didn’t.  She greatly enjoyed the roleplay and fantasy aspect of things.  Hence why she continued, even though deep down it was an escorting thing.  I mean I was going to shoot my shot again, but we were both content with how things stood.  

So yeah, that’s my story.  I probably left out so many details.  Happy to answer if there’s enough interest or questions.

Source: reddit.com/r/gonewildstories/comments/10x7xfs/i_accidently_turned_an_ig_model_into_an_escort_mf