Chapter 7: Something In The Air, Part 1

Ben

This year really flew by, it’s already well into September, but at least it’s still nice and mild. Even though the calendar says Fall begins in a few days, we’re still getting plenty of summer-like weather. It’s all good, the longer the warmth hangs around the better.

My job at the National Fruit Distribution Company is going well; I’ve been promoted to department manager in charge of blueberry shipments. Now I can afford to start looking at a better apartment and maybe even start saving up for a house.

It seems like just a couple of short weeks ago my younger brother Will was graduating high school. He’s been having quite a summer and started dating his first girlfriend, Daisy. I met her at our parent’s house; talk about cute-as-a-button, wow! She’s one of those girls you can tell has a white-hot fire burning under all that cuteness and is probably an unleashed wildling once you get her in the sack. And, then to find out she’s an escort! Sex is her profession. He’s one lucky son-of-a-bitch, that’s for sure. (I gotta watch affectionately using son-of-a-bitch when talking about Will, we’re from the same parents after all!)

Don’t get me wrong, I have the coolest little brother a guy could ask for, but damn, I would be lying if I didn’t feel pangs of jealousy when I think about how he met Daisy at a sex party with four hot women. Four! Having multiple women has been a fantasy of mine since I first started stroking myself. I was shaking my head in wonderment when he told me he couldn’t remember how many times he came that day. Lucky bastard!

My life is good and I have no room to complain, I have a great thing going with my girlfriend, Sandy. We met a few months ago and couldn’t be happier. A much better choice than my previous lover, Christy – well, we were more fuck buddies than true lovers.

Christy was an absolute trip, talk about super easy to get in bed, too easy actually, we did everything, and I mean everything, on our first date; but other than a lot of great sex, we just didn’t have much else in common. Over time we drifted apart, she started screwing other guys and I started looking elsewhere. I wasn’t broken up about it or anything, Christy just wasn’t the one for me, or me for her, that’s all.

Sandy and I connect on so many levels. We like the same music and movies, she loves roller coaster parks as much as I do, and we even enjoy the same kinds of foods. To top it off, she made me work for it. When sex with Sandy finally happened on the seventh date, the wait was well worth it. With our bond growing, it’s now a regular part of seeing each other.

We’re going to a nice dinner event tonight; it’s her company’s annual party. It’s semi-formal and she says I don’t need to wear a full suit, but a nice button shirt and dress pants will work.

Even though I have my apartment, I still come home to Mom and Dad’s to do my laundry. The machines at the complex suck big time, even when they aren’t needing repairs. Dammit, I forgot to bring my dress shirts to wash, and I don’t have time to run back. Will and I are basically the same size, I don’t think he’ll mind if I borrow one of his.

When I go looking for him, Mom says he’s out again with an eye roll. Apparently, Will has been spending a lot of time away, pretty much every weekend with Daisy. I wonder how that works, I would imagine weekend nights would be primetime working hours for her being an escort and all. I’m not sure how I would feel about my girl screwing other men even if it is for good money. Not my horse, not my race; in other words, to each, their own. It must not bother Will because the two of them have been together for a while now.

In Will’s closet, I search through his hanging clothes and - wait, what’s this? There are about half a dozen three-piece suits hidden in the back. Stephano Ricci, Indochino, Brooks Brothers, these are not cheap suits. What the hell does he need all these fancy clothes for? He’s a typical jeans, open flannel, and white t-shirt country kid. Finding a nice blue dress shirt, I pull it out; I’ll have to ask him about this buried treasure of fine attire next time I see him.

A couple of days later I’m having lunch with my buddy Owen at Lorna’s Bar and Grill; you might remember him from that party at Josh’s house when we helped make Heather’s fantasy with multiple guys come true. Owen is an assistant manager at Big Woody’s Lumber & Hardware, the same place my brother works. As we dive into our juicy burgers, I ask, “So, how’s Will doing at the store these days, everything good?”

“Oh, yeah, Will is super, one of our best. I just wish I could schedule him for more hours.”

“Are things slow right now?”

“No, it’s not that. He only wants to work one or two days a week. Usually a Monday or Wednesday, and no weekends when I could use him the most.”

“That’s odd. I figured he’d want all the hours he can get.”

“That’s what I would think too,” Owen shrugs.

After lunch, I’m perplexed with what’s going on with Will, things aren’t adding up. College tuition, car payments, auto insurance, about four to five thousand dollars’ worth of suits tucked away in his closet, gas to drive to and from Holland every weekend, how in the fuck is he affording all this and only working one or two days a week? Did he secretly win the lottery or something? I think it’s time for a little brotherly one-on-one chat.

When something doesn’t make logical sense, it bugs me until I figure it out. I’m one of those people that likes to solve puzzles, any kind of puzzle, in its own way it’s entertaining and keeps my mind sharp. Murder mystery movies and books are my favorites, but all too often I guess the culprit way too soon.

I’ve been turning over possibility after possibility as to why Will seems to be so financially secure and working so little. Did he get into stock trading and luck out on a windfall? Is he gambling and striking it large? Those suits: he’s always hated dressing up. Why Now? Why is he so interested in dressing like a gigolo?

A gigolo? Nooo ... it can’t be. Can it?

Call me crazy but has he taken up working in the same profession as Daisy? He is a good-looking guy with a calm gentlemanly demeanor beyond his years; I can see how women would take to him well enough. I hate that my mind is drifting in this direction, but it’s the only thing that makes sense. He would need to be presentable to well-to-do women who can afford to hire a male companion; that would explain the suits. This also can explain all the weekends away and why he’s seemingly okay with his girlfriend regularly having sex with others - he’s fine with it because he may very well be doing the same thing!

I may not know much, but I do know escorts and gigolos can make an ass-load of money. If this is true, he probably doesn’t even need that job at Big Woody’s but keeps it for appearances, hence the minimal hours.

This has got to be it, nothing else completely answers all my questions so concisely. The icing on the cake is how Will has been walking around with a perma-grin plastered on his face and a profound new sense of confidence, he’s almost a bit cocky at times. Although, this can be attributed to the fact that he’s now having sex regularly, a lot of guys go through such a phase with their first girlfriends. But if he has people actually paying him to fuck them, what kind of boost to a young guy’s ego would that be?

The next day, I pull into the driveway at Mom and Dad’s. Will’s car is here; good. In the house, he’s watching TV and Mom and Dad are out; perfect. I grab a couple of bottles of Pepsi from the fridge, hand him one, and plop down in a stuffed chair across from him.

“So, I borrowed one of your dress shirts the other day, the blue one.”

“Yeah, Mom told me, it’s fine,” he answers, not looking away from the TV.

“I couldn’t help but notice the luxury menswear department hidden in the back of your closet.”

This gets his attention; he pauses the TV show and sits up. “Oh, that ... uh, yeah, Daisy likes to ... um, Daisy likes us to get dressed up and go to fancy restaurants and stuff.”

“I’ll bet she does.”

Taking a mildly defensive tone, he asks, “And what’s that supposed to mean?”

“Will, you’re a bad liar, but that’s a good thing, it’ll help keep you out of trouble.” He looks at me unsure what to say and unsure what I know. Skipping beating around the bush, I just come out with it. “Will, have you been doing things ... doing things similar to what Daisy does?”

He’s quiet for a bit, then a tiny smirk forms on his face followed by a muted, “Yes.”

“I knew it!” I snap my fingers in self-praise for correctly sleuthing out this mystery.

“But ... how do you know?” he asks incredulously.

“A lot of little things that didn’t add up. The expensive suits, the newer car, insurance payments, college tuition, and when I found out you’re only working one or two days at the lumber store, I had to ask myself how is he affording all of this? I got to thinking about Daisy, and what she does, and I could only come to one conclusion that connects everything; he must be working as a male escort.”

“Please-please-please, keep this a secret, Ben. Mom and Dad would kill me if they knew.”

“Look, we’ve always been super cool with each other, better than most brothers, your secret is safe with me. Just tell me you’re being smart and safe about this.”

“I am...” he breathes a visible sigh of relief, “ ... and thanks.”

“You need to find a better place to hide those suits. The last thing you want is Mom or Dad asking questions.”

“I know, I just don’t know where—” then he snaps his fingers and asks, “Could I keep them at your place?”

“Sure.”

“Cool! Thanks!”

“Absolutely,” we fist bump, then I ask, “Are you allowed to talk about what you do?”

“To an extent. Why?”

“Just curious. I mean it’s not every day you find out your little brother is getting more ass than a toilet seat ... and getting paid on top of it.”

“Well, I guess that surmises it pretty well,” he laughs, “I can only talk about things in a generalized manner.”

“Works for me.” This is so strange, I’m eight years his senior and here I am tuning in like a salivating ten-year-old just discovering porn on the internet.

I think Will has also been wanting to talk about this because he wastes no time launching into his story. “Well, it all started when Josh’s friend Heather came into Big Woody’s after that day at his house. We went out to lunch and talked about how she wanted to repay him by fulfilling a fantasy of his. Josh told her he’s always wanted to experience several women doing him at once, like groupies on a rockstar.”

“What guy hasn’t,” I add.

“No kidding,” he agrees. “Heather has a business client with connections to an escort company.”

“Is this the company you’re with?”

“Yes. The woman owns a beach house on Lake Michigan. She arranged for three of her escorts to entertain Heather’s party and even granted use of the place. Being that we both came up with the idea, Heather wanted me involved. I was apprehensive at first, but she coaxed me to join.”

“Apprehensive? Dude, we’re talking about an invite to a sex party with a two-women-to-one-male ratio! What’s to be apprehensive about?”

“Well...” he shrugs, “it was still early summer, and I was a lot shyer back then. Even doing Heather with all of you guys at Josh’s house made me so nervous. Plus, Heather said she wanted to see my adorable I’m cumming face being she was blindfolded.”

“Oh, I’ll bet your O face is absolutely precious!” I tease, and then mimic an exaggerated orgasm complete with hip gyrations and moaning, “Ohh! I’m cumming! Ohh! Ohh! Ohh!”

“Alright, enough! Fuck off,” he laughs.

“So, what kind of things happened? I remember you told me you came so many times, you lost count.”

“And that’s true. My first load was in one of the girls’ mouths and then, get this, they all passed it around from mouth to mouth so each could have a taste. I have never seen anything like that in my life! And they weren’t done with mine because they did the same thing again when Josh came.”

“Wow! Snowballing, it’s called. I always thought it was just a porn gimmick, who knew it actually happens in real life?”

“Dude, the whole day was like living in a porn movie. Josh and I alternated fucking all the women and eating them out, all the girls sucked and fucked us, it was crazy wild! Daisy took the lead with fun games like whose precum tastes the best, whose pussy tastes the best, and things like that. Pretty much everything that happened was a great big first for me!”

“Wow...” is all I can utter. “So how did you and Daisy end up hooking up afterward? Like I even need to ask...”

“She said she liked me because I seemed more mature than most guys our age ... if you can believe that,” he shrugs.

“She’s right, you are ... but don’t let that go to your head,” I joke.

“Oh, trust me, I’m becoming an expert at not letting things go to my head. My new life is one great big exercise of keeping my ego in check. Anyhow, Daisy was passing through town a couple of weeks later and hit me up. She picked me up from work and we went to that little motel over on Route 11—”

“The Silver Crest!” I chime in. “I know that place, Christy and I went there all the time before I got my apartment. We called it the Silver Crust because of all the crusty cum stains we left on the bed covers. Hahaha!”

“Thanks for that visual,” Will rolls his eyes, “but yeah, that’s the place. While we were there, Daisy got a text from a couple looking to have fun with another couple. At the time there were no male escorts, so Daisy asked if I wanted to fill in ... and I did. We met up with the couple at a big hotel in downtown Grand Rapids, had dinner and drinks, and then it was onto the sex.”

It’s unbelievable listening to him, is this really my brother? It’s like he’s been granted special access to the super-secret sex-filled underworld!

“The night went really well, and the couple left glowing reviews for Daisy and me. This got the interest of her boss and she wanted to meet me and see if I was interested in becoming a male escort. Daisy said I was a natural. We met at the company office for a job interview ... of sorts.”