Chapter 27

Will

A couple of hours ago Jasmine called to let me know it’s time to dive headfirst into this Swim Club thing, she’s set up my first paying date with her longtime friend Vicky. Now that Jasmine has added her to the secure Swim Club app, we can communicate to make the arrangements.

I introduce myself, “Hello Vicky, I’m looking forward to meeting you. What sort of fun are you looking for tomorrow evening?”

A brief pause then she replies with, “I want you to fuck me, you should know that.”

“Yes, there’s that, but is there anything else you would like to do?”

“If you’re talking about a fancy dinner and dancing? Nah, not interested. I just want to meet up and do the nasty.”

Do the nasty, sounds like an old-school 80s rap song. “Do you have a preference for a hotel or motel?”

“Anything with a bed is fine.”

“How about the Silver Crest on Route 11?”

“That’ll work and I know where it is. Let’s meet there at 7:00 tomorrow.”

“Perfect! I’ll get us a room when I arrive.”

“Don’t go getting all dressed up on my account or anything like that. Wear your jeans, flannel, and work boots, however you’re comfortable.”

“I can do that.”

“Oh, and underwear like in the pics Jas sent, I like that bulge.”

I have to snicker at that. “Sure will!”

Alright, we have the time and place. I shouldn’t have to make any excuses about being gone overnight since the motel is close and I can be home after slipping Miss Vicky the sausage.

All day at work I keep thinking about how I have my first client tonight. I have a woman paying me to fuck her. I can’t get over that, it’s surreal.

Following a shower, I put on snug boxer brief underwear like the ones I wore in the pics. A look in the mirror confirms I have a nice-looking shapely bulge to show off. Blue jeans and a plain white t-shirt with my red plaid flannel as an overshirt complete the requested look – it’s my everyday look anyway.

At the Silver Crest Motel, there’s an older model dark red minivan in the parking area with a woman waiting, that must be her. She’s in her late forties to early fifties with brown hair starting to gray pulled back and tucked under a trucker ballcap. She’s carrying a few extra pounds and her looks are very typical of an average middle-aged woman. It’s hard to picture Jasmine and Vicky hanging out as friends because they seem so vastly different. This woman is every bit of a tough blue-collar hard worker type that probably spends most evenings shooting pool with the guys at the local VFW Hall and drinking Pabst Blue Ribbon beer. Jasmine, on the other hand, spends the same evenings fine dining at a place like Chez Louis’ Chop House in a fancy Ritz-Carlton Hotel.

“Are you Vicky?”

“Only if you’re Will.”

“I am. It’s wonderful to meet you,” we firmly shake hands. “Let me get our room all set up.”

“You do that. I’ll wait right here.”

In the motel lobby, of course, Betty-Jo Peterson is working again. “Well, well, well, aren’t you the familiar face around here. Maybe you should rent at the weekly rate, it’ll save you money.”

“Tonight only, please.”

Fighting off laughter, Betty-Jo flicks her thumb towards the window at Vicky waiting out there. “Are you doin’ your girl’s mother now, or something?”

“Just ... never mind, it’s a long story.”

“I like a good story,” she grins. “Come on, spill it.”

“Sorry ... no. Not gonna happen.” I grab the room key and rush out.

At first, my thoughts were that Vicky not wanting to be wined and dined would make this date a breeze, she just wants sex, but here we are, two complete strangers sitting on the bed, staring at the wall and wondering what to do next - talk about awkward. Small conversation over pizza or even fast food would’ve helped give me some sort of starting point to work with.

I’m reminded of what Daisy told me about playing the vibe of the room. What I know about this woman is she’s direct and isn’t interested in any cutesy charming fru-fru-ey nonsense. I guess I’ll just get right to the business at hand. Already knowing she wants what’s in my undies, I can be direct as well. Standing up in front of her, I ask, “Do you want to undress me, or have me do it?”

“You take your shirt off.” With a tiny grin, she adds, “But I wanna pull your pants down.”

“Works for me.”

Kicking off my shoes, I remove my flannel and pull my white T-shirt over my head, Vicky nods approval of my naked upper torso. She reaches up, undoes my belt, and opens my fly; I can’t resist pushing my pelvis forward so her hand rubs over my bits as she lowers the zipper. This is becoming a trademark move for me, I snicker to myself.

Down go my jeans and I step out of them, the whole time her gaze never wavers from my bulge. “Ah, you’re a good boy, Will. This is exactly what I wanted. I’ve always had a thing for guys showin’ off their bulges.”

At the risk of being a bit cocky, I push my hips forward. My cockiness pays off as Vicky grabs my waist to pull me the rest of the way, smashing her nose into my squishy genital pillow. Rubbing her face left and right, up and down, mashing in and drawing back, she’s deeply enjoying my hot place. To her, it’s as if I’m fresh catnip to a ravenous kitten indulging for the first time. Her lips are opening and closing on my front swell as she’s exploring the tubular shape of my dangler and the spongy roundness of my bean sack. It’s a real turn-on watching her fascination.