Author: SweepPass44

2 Instagram Models snowballed my cum [MFF]

One of my favorite Instagram Escorts to book is this model Lisa. Really chill, down to earth, very sexually open minded. Other than our business arrangement, she’s cool to hang out with, which makes things so much easier. We’re friendly with each other, more than a client provider thing, but not BFFs or anything.

A little bit ago, Lisa reached out to me, and asked about booking directly with her. Sure, of course, would love to sidestep the cut throat bitch Madam that I usually have to work with. But Lisa asked for a favor. One of her model girlfriends, Emma, was looking to ‘get into the business’. She wanted to tag along to a date, and see how it all went down. Lisa asked if I was cool if Emma can tag along and watch. Fuck yes, absolutely. Would love to fuck, and have an audience. I wouldn’t get to play with Emma, but that’s perfectly fine with me. Read more »

I hired an Instagram escort to help close a business deal [MF]

Part of my job involves closing and landing business deals. Some deals are straight forward, some are drawn out, with some schmoozing and wining and dining. I like the challenge, and the sales rush and all.

A while ago, I had this major prospect in the pipeline. Would have been a huge deal for me, if I closed this. The point person I’m working with, he’s a nice guy and all, but he’s this big shit and knows it. Which makes it even worse. But it’s part of the business. Anyways, we’re going through the pitch, and our numbers/proposals are very competitive to everybody else. Honestly, a coin flip either way. But he’s not budging, he likes being courted and sold, so he gets all the attention.

One day I happen to follow him on Instagram. And I notice that he’s creeping on all these hot instagram models. Commenting, messaging them. He has no online game at all, but you can tell that all he does is follow and creep these models. Then I notice one that he’s fond of, a model that I previously hired for my own fun. Lisa is this blonde bombshell. Girl next door with huge fake tits and an outgoing attitude to go along with it. Boom, that’s my in. Read more »

I accidentally used my corporate credit card to book an Instagram escort. [MF]

Officially, the statement charge was “Food and Beverage”.

I had a date with an Instagram escort. We were introduced by a mutual friend, the madam that I’ve connected with. By this point, I had been a loyal client. Always discrete, always respectful, no drama here. I had given them so much business – if there was some Rewards Points system, I would probably be on the super elite status level.

I arranged for the date to coincide with this business trip I was on. We were hosting a conference/meetings, so my corporate card was in full use. With normal expenses, I just have to submit a report to my job, to reconcile everything. It’s not perfect, especially with large conferences like this. My card was used for everything big or small.

Anyways, date night arrives and I meet my girl. Young, pretty, any man would be happy to fuck her senseless. I’m ready to reconcile with them, but I realize that I didn’t prepare my payment in advance. In all the craziness of the convention, I forgot to line up my funds to make the night’s transaction occur. I’m not the type who misses something like this, especially for such a discrete night. So I’m a bit embarrassed and annoyed at myself. Read more »

You know the world is crazy when your Madam sends you a Covid-19 update [MF]

I must have received dozens of Covid-19 “What we’re doing” emails from every single company. Hotels, airlines, my gym, etc… As expected, I guess.

But shit got real for me a little while ago, when I got a similar email from this woman I’ve been working with. She’s a madam, and sets up ‘dates’ with escorts. Finding her was a game changer for me. It wasn’t so much a “What we’re doing” email… more like a pre-canned copy and paste. Saying that things are shut down for the time being.

Sure, I’m flexible and I get it. We are all in this. But it’s killing me. And I’m sure it’s killing her business and the models’ income as well. But better safe than sorry.

I’ve been texting some of the model ‘providers’, just checking in and all. And basically they don’t know when they’ll be back working. But whenever that happens, they’re going to go bananas. Book as much as possible, to make up for the lost time. It’s kinda of surreal to read/chat knowing that this woman wants to be a human fleshlight for men like me. Non-stop, every night, whatever I’m into, she’s into, just so long as business keeps on coming in. Read more »

I fucked an Instagram Escort in front of my coworkers [MF]

There’s the semi-famous hotel downtown that has huge floor to ceiling windows. It overlooks an office building, a busy street, some apartments, etc.. The hotel is known for its guests fucking in front of the window and giving the voyeurs a free show. I’ve worked in that office building before, and we’ve all noticed when we see a couple playing. It basically shuts down the office and mostly everybody watches on. Like we all text each other to alert them of a show.

I was traveling for business, in New York City. When I found out that I had meetings in the office building across the street, I thought it would be hot to arrange for a little sex scene, where anybody can see. So I booked a room, I asked for a high floor so our faces couldn’t be recognized. Then I booked the Instagram model. Anna is a girl that I’ve booked before. Tall, blonde, blue eyes, huge boobs. All American girl next door type. You would never know she’s an escort on the side, which makes her even hotter. She is a kinky, adventurous woman, one of the many reasons why I keep on booking her. Read more »

My secret life of hiring Instagram Escorts [MF]

Saw the Sub’s monthly writing challenge, so I figure I would give it a shot.

I’m the over achiever type of guy.  Always gets his shit done, puts in long hours at the office, dependable, reliable, etc.  As such, I’ve advanced my career, sometimes priortizing that ahead of family and friends.  Yeah, I know unhealthy, but you all probably know someone in your life that’s simliar.

The thing is, I have the secret kink of hiring escorts.  Like all the fucking time.  It started about a year ago, and it’s been non step ever since.  And it’s not like I’ll hire any escort.  No, I go for the top talent.  The Instagram model escort.  The 10s.  I’m such a boujee client, when it comes to models.

I travel all the time for work.  I recently got several promotions and moved up the corporate ladder.  So that gives me flexiblity, both in time and travels.  So whenever I travel, I often bring a girl along.  A traveling fuck date, so to speak.  Our travel department allows execs to bring someone, to tag along.  Other work colleagues bring their spouses.  Or their kid, so they can sight see.  No, not me, I bring a model escort to play with.   Read more »

I shared an Instagram Escort with one of my friends [MF]

I have a bad habit of hiring Instagram models as escorts.  I have a stressful life, caring for some family, while juggling a very demanding job.  I find that these ‘dates’ are helpful for me to decompress, unwind and relax.  Albeit for a short amount of time.

A little while ago, I brought an Instagram model to one of my office parties.  We had fun socializing and later that night we had some private fun.  A few days later, one of my work colleagues, Chris, approached me.  Chris is a very good friend of mine.   We started at the company at the same time, and share many of the job’s stresses and challenges.  He’s way higher up in the company and makes a ton more money, but all good, he deserves it.  Not only do we hang in the office, but we chill outside with sports and whatever.  So Chris approached me, and recognized the model.  Asked what the deal was?   Read more »

I was an Instagram Escort’s first client [MF]

See my posting history for background.

Usually when I connect with an escort, I just pick from what’s available to me. Really, I’m not a picky person, and these women are all out of my league anyways. But a little while ago, I had the opportunity to actually pick the specific model that I wanted.

I’d like to think I’m a good client/customer. Respectful, private, clean, repeat business, etc… All the qualities one should look for I guess? So I was chatting with this Madam and asked her if she had any new models she’s working with. Someone new, fresh and different. Being the private person that she is, she didn’t really respond. So I suggested someone to her, someone that I was secretly was hoping was in the business. I didn’t think that she way, she had that wholesome girl next door type of look. Which made her even more attractive to me. Again, the Madam didn’t say anything, and I just dropped the whole conversation.

A few weeks later, I’m speaking with the Madam, and setting up another appointment. After the usual chit chat, she mentioned that my before mentioned model IS available. Holy shit, dreams really do come true. I’ve been hoping and dying for the opportunity to fuck her silly. So after the usual logistics of planning and stuff, we set up an appointment. Read more »

I brought an Instagram Escort to my office parties [MF]

I know you shouldn’t mix business and pleasure. That’s the logical thing to do. But when you’re under a lot of stress and can’t keep it together, sometimes you do some stupid shit. That’s exactly what I did not too long ago.

My work is really stressful. Competitive, have to hit numbers/goals. We’ve gone through a bunch of mergers, and with that comes layoffs and new expectations. You corporate America folks probably know what I’m talking about. I work in an industry that’s like 90% male. They’re single, make a ton of money, and living the ultimate bachelor life. So the culture could be very macho. Which is fine I suppose, but just giving you context.

We have these work parties periodically. Well it’s not really a work party, just a guy hosting some work friends at his beach house or something. These guys are competitive with the women that they bring. Some kind of weird alpha dog trophy girlfriend type of show. In the past, I didn’t really like going to these parties. Don’t get me wrong, it’s cool to hang and chill. But I don’t really need the grief my friends give me, when I show up solo. Read more »

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. Read more »