Chapter 38

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.”

“Of sorts?” I ask.

“Ummm ... just to ... you know, go over details ... the ins and outs.” I get the feeling more happened than he’s letting on, but he’s choosing to keep quiet about it. Probably a lot of ins and outs.

“So, you accepted, I assume.”

“Yeah. This all happened around the time you met Daisy. We figured introducing her to Mom and Dad as my new girlfriend was needed as a viable excuse for me being away overnight and often.”

“I remember that day,” I nod.

“Once I was hired in, the dates began.”

“I know you can’t say too much, but what kind of dates or people hire you?”

“Clients, we call them, and all kinds really. Most are middle-aged older women. I did have a date with a couple in their mid-twenties. The girl wanted to experience two guys at once, so it was me and her boyfriend. I had a charming elderly lady in her seventies, a true sweetheart of a grandma, and she was so thrilled with a night of fun. I spent three whole days at a business convention with lots of horny traveling businesswomen to please, made a ton of cash that weekend—”

“Is it all just fucking, or do they want to suck you too?”

“Both. It’s surprising to me but most clients want to have a suck. At first, I thought blowjobs would be a special perk of the job only happening once and a great while, but, no, it’s actually a very common request. What helps is a little routine I learned from Daisy of letting them undress me; it works like a charm for getting them all ... hungry for it ... if you know what I mean.”