It was $100 every time. She’d finish up, hand me the crisp bill and wave me off to leave her to compose herself before she went back to her lounger on the pool deck. I never once felt bad for taking her money, wealth dripped off of her, and besides, I was broke.

I was 22, just getting by, eating mostly instant ramen and instant oatmeal, putting all my money towards text books and rent. As summer jobs go, the country club wasn’t that bad, and the additional $100 or more per week from Mrs. Ava Spencer was a welcome windfall and all I had to do was keep my mouth shut. She was stunning, the sort of woman whose whiteness and wealth was so glaringly obvious that she positively glittered with the spoils of privilege: flawless in the details, she was manicured in all regards to an almost doll like degree. I’d heard the folklore in the staff lounge about her and her appetite for ‘premium service’. That’s what the guys called it. They mocked her in secret, but they all clearly wanted to be one of the chosen ones, I could tell by how they ribbed the guys that claimed they’d made extra cash in the past catering to her whims. At first, I couldn’t believe the rumours were true but after watching her I could see how they might be. She didn’t bother with the lifeguards or the guys that taught the poolside work outs, they were too often accompanied by throngs of teenage girls with summer crushes. No, Ava played it cool. She kept to the wait staff and bartenders, the cabana boys and the valets.

She was easy to spot: always in a black two piece, always lipstick, usually red, oversized sunglasses and a broad rimmed hat. She had an golden-age-of-Hollywood vibe, like I said, she was old money and looked the part. No matter which shift I was on, she seemed to be there most of the time, sunning herself, sipping strawberry daiquiris and swimming endless laps in the pool. I’d like to think that I noticed her before she noticed me since her reputation preceded her, but looking back, I think that she was more than a few steps ahead of me.

My first encounter with Ava Spencer was brief and direct. That was her style. It was a brilliantly bright and hot July morning and The Ladies (that’s what we called the women who tipped most generously) were just trickling in; rich housewives stopping in for a dip after their tennis lessons, before Pilates or whatever other luxurious activity they filled their time with. I was delivering a tray of smoothies to guests by the pool that morning when she caught my eye and beckoned me over with a nod. Smoothies dispatched, I crossed the pool deck to her chair and crouched down to her level, smiling, introducing myself and giving a coy salute. To my surprise, she smiled, and almost chuckled.

“I’d like a mimosa, please. Very cold, and keep them coming.” She plucked a $50 bill from her impeccable cleavage and held it out between us. “And there’s a tip in it for you if you meet me in cabana 9 in 10 minutes.” She lowered her sunglasses and peered at me over the rims. “Do you understand?” I swallowed hard and nodded. I was instantly nervous, not really knowing what awaited me in cabana 9 and a bit baffled that the rumours were true. I was even more baffled that she’d picked me out of the crowd. I wasn’t the tallest guy or the most hard-bodied, certainly not the most handsome. I was however, broke, and mesmerised by the bill she tucked into the pocket of my shorts. I smiled and nodded and repeated “Ten minutes, cabana 9.” She smiled back and I was dismissed.

Nine minutes later my palms were sweaty and my mouth was dry and I was hyper aware of the way the $50 bill crinkled in my pocket. I had no idea what she wanted with me, the rumours were always vague or so overblown that they were unbelievable. I checked that no one was watching, knocked softly and heard the cabana door unlock. I took that as my invitation and I stepped in. Now, these were not just tents to change in. Each one was a stand alone room complete with sink and toilet and shower, comfortable teak benches, and frosted skylights. The ambience in them was as nice as some hotel rooms, if not nicer. Additionally, they were air conditioned and well insulated for sound. I stepped in and closed the door behind me.

Ava was perched on a bench in a robe, eyeing me intensely. She didn’t speak, she simply pointed for me to sit down as she undid her robe and leaned back. I sat, wide eyed and watched as her robe fell away and her hands slid between her legs. She locked eyes with me and it seemed rude to look away but also not appropriate to ignore her undulating nakedness, which was clearly why I was there. I swallowed the panic at the thought of being told to touch her or pleasure her, and thought about the money. I watched her and that seemed to be all she needed me to do. She spread herself and dipped her fingers inside of herself, slathering the tender-looking pink skin of her lips with the glossy wetness that was slowly trickling out of her. Her tits were smaller than I expected, but beautiful, faint tan lines decorating their tops and sides as they jiggled and swung with her masturbatory efforts. I had never seen a woman touch herself so casually without pretence or shyness. It was fascinating. She was fascinating. I was filled with questions I knew I couldn’t ask. She plucked at her nipples as she approached orgasm, her body writhing more quickly and less sensually as if she’d passed some magic threshold where performance had turned to focus. Faster and faster she pressed and rubbed and plucked and slapped until her brow was knitted and her lower lip was clenched in her teeth. She came hard, nearly silently, looking me dead in the eyes. She flooded the bench and floor below her with a triumphant and body-quaking squirt, and slumped back, fully relaxed. I waited, unsure what to do.

“The money is on the counter.” she waved an arm in the direction of the sink and shower and closed her eyes.

“You already paid me, ma’am …” My voice came out small and soft and my cheeks burned with confusion and embarassment.

“That was just to get you in here. But I see you didn’t enjoy yourself much so we don’t have to do this again.” She said this while eyeing the distinct lack of erection in my khaki shorts. I could feel the sweat on my back.

“Oh, that’s …. uh … that’s not about you. I just don’t …” I stammered and she cut me off.

“You’re gay?”

“Something like that.”

“I don’t mind if you don’t mind ….” she smiled. I smiled back.

“Look,” she said plainly, “I don’t want an affair even though I hate my husband and he’s terrible in bed. This,” she waved a hand to indicate the strange sexual covenant we were suddenly in, “this is what gets me off. And I’m willing to pay for it. One hundred bucks a pop, three days a week. All you need to do is watch. But you have to keep your mouth shut.”
I took in her words and strangely, they didn’t make me suspicious. I trusted her or at the very least I trusted that I wouldn’t have to do more than watch. She extended her hand to me to shake it.

“Do we have a deal?”

I paused, my fingers idly folding the $50 in my pocket and eyeing the one on the counter.

I shook her hand. “Deal.” She smiled as we shook hands. “There had better be a mimosa by my deck chair by the time I’m done showering.”

“There will be. Ice cold, and I’ll keep them coming.”

She handed me the second fifty dollar bill, still naked, not a smudge of makeup or a hair out of place and grinned.

“See you on Wednesday, Pool Boy.”

“My name is Peter …”

She smiled again and said, not at all unkindly, “Oh. How nice. I prefer Pool Boy.”

I didn’t argue. I thanked her for the cash, and backed my way out of cabana 9 with a big secret, bewildered, enlightened and a hundred dollars richer.

Masturbation Monday

logo for The Blog Days of Summer, and erotic writing prompt for August

Violet Fawkes

Violet Fawkes (she/her) is a freelance writer and sex blogger focusing on pleasure education, erotic fiction, and the intersection of identity, kink and mental health.