Chapter 5: The Oldest Profession, Updated

As I mentioned, my home and my mother’s workplace, as my sexual journey began, were in a suburb once considered “in the mountains”, a place for resorts. Our place had been one of the small resorts. A number of the larger ones had become assisted living communities.

How can prostitution be the oldest profession? How would the customers have earned the fees?

For a given engagement in the sex industry, we called the project/engagement leader the producer. A senior producer might manage continuing engagements with the same client.

Mom knew the director of nursing at one of the retirement communities. Working with her as a senior producer, the management of the community was introduced to me as line producer. Stella was my contact as line producer. I knew that some fantasies were very common, but wanted to be sure there were no misunderstandings, especially when younger workers were involved.

They agreed that in the moderate term, it was simply too risky to involve young workers with residents who had any level of dementia or other cognitive impairment. They had gone through notes and personal experience, and identified residents who had flirted strongly, or showed outright sexual interest, in the nursing staff. With Stella. the nursing director, initiating conversations, they established who was willing to pay for naughty nurse services, and how the client would recognize the sex workers as opposed to the regular health care workers.

Mother, daughter, and Charlie, a great old gentleman

Charlie was a nice old man, in assisted living and generally unable to leave his room. His daughter, Carlotta, arranged for Mom to make a call, aa a young assistant. She was to be the athletic director and I would be a cheerleader. The script was simple; he was a beloved teacher we were visiting and wanted to make happy. One of the facility’s nurses would be present, and both part of play but available if he got any physical trouble.

Cheerleader fantasy

Mom explained, “The fantasy of this gentleman, and probably several others, was to be visited by the gym teacher, who would show him a cheerleader, gymnast, or other teenage but legal athlete, in a revealing uniform and provocative makeup. Both women would have wardrobe malfunctions and touch one another in interesting ways. His fantasy was to masturbate while watching them, without their noticing. In other words, he didn’t want to be perceived as a peeping tom or other dirty old man.

“If we have more than one person who wants this, Cath can be the teacher for it. Right now, you’re our only cheerleader that’s truly that young, but we’re working on more. The fact that you’re younger than Cath is irrelevant for the engagement management.”

“Gee, Ada, I’d be more than happy to masturbate him or otherwise get him off.”

“I know, Annamarie, but this is what he wants.”

Stella chimed in, “Others want exactly that, so treat this as a warmup.”

●●●

My red and black cheerleader outfits were more NFL than high school, with heeled knee boots rather than sneakers or oxfords. It exposed tight midriffs. Under the short skirt were black panties with an easy-release waistband.

Ada’s outfit was closer to dancewear, with a leotard cut high on the hips, and low in the front, with a zipper from neck to crotch. Underneath, she wore black crotchless tights, where her mound would be revealed if she pulled down the zipper, yet her legs would be in the wet-look black.

With Mr. Vargas

Stella, Ada, and I went into Mr. Vargas’ room. He greeted us with smiles. “Going to beat those football wannabes at Washington this weekend?”

“Sure!” (We had no idea of the rivalries. Will have to check that before our next date.)

Cath sat to talk to him. She carefully crossed her legs, letting her skirt rise. “Annamarie came with me to show you our new uniforms.” Without comment, I started to fidget with the zipper at my neck. “See her spins and cartwheels?” I went into a toe spin, causing the skirt to flare to waist level, showing off her quite brief panties.

I’d been practicing my gymnastics beforehand; it wouldn’t have worked if I got dizzy and fainted. The room was large enough for a cartwheel and some deep bends. On the second cartwheel, I hit the concealed waist catch, and the panties fell to my ankles. I made sure to be pointing my crotch at him, apparently unaware that anything had fallen. I turned around and bent forward, giving him a great look at my naked ass.

Stella whispered to Ada, “That’s making me hot. I’d like a taste of her ass.”

“That can be arranged among friends.”

When I stood upright again, I could see his hand, busy over his sheet-covered groin. Without making eye contact, with seeming innocence, I ran my fingers over my labia and clitoris, as if scratching an itch.

Stella

After leaving, Ada started to explain, “Stella was appreciating you...” when Stella grabbed my hand and pulled me into an empty patient room, gestured with her head to Ada, and, as soon as the door closed, swept me into her arms. She had been wearing a lightweight white coat over a maxi dress.

Stella had a really pretty face, with moderate makeup. She was tall and tanned. Her hips were substantial, not grotesque but more than she would like. Breathing hard, she moved her mouth against mine and plunged in her tongue.

Ada called out, “Don’t worry, this is on the house among friends!” Pulling down the zipper as she sat, Ada was soon sitting on a couch, fingering her almost bare mound, with a bright red landing strip.

Annamarie reflects on production

“What did you learn from that, Annamarie? It was, after all, your first paid engagement.”

“It was difficult to ignore him masturbating, although I know that’s exactly wanted. He’d be embarrassed if I noticed.”

“Yes.” Stella amplified, “There are others that are nastier. They want to know that you see them masturbating, but it embarrasses them. Their ignoring it is, to some extent, submitting to their control.”

“I did like showing off, if rather discreetly. There’s little question in my mind that I’d enjoy some blatant exhibitionism with at least solo sex play. Mom, this sort of thing seems to run in our blood.”

A little riskier: Mr. Millard

“It’d just as well we moved into this room, because this is where I stashed your changes of outfits.

Stella and stock fantasies

Moving into more risk, although none with you being consensual,” Stella told us, “involves nurse rather than cheerleader fantasies. The men want at least to look up nurse uniforms, enjoy a view where there’s a wardrobe malfunction, and, eventually for some, feel us up underneath while they masturbate. A variant is lesbian play among the nurses, as a voyeuristic stimulus. Others actually want to admit there will be sex among the participants.

“Some fantasy nurse outfits are absolutely ridiculous, and I can’t play with one. Red rather than white skirted uniforms, for example. Latex or PVC -- those belong as outright fetish. No, I go with white or navy skirted uniforms, which can have very short skirts and revealing tops. Yes, we can do candy-striped or light blue student outfits. White stockings for both. Sexy shoes that would kill the feet of real nurses, but fine for fantasies.”

“OK, ladies. Annamarie and I need to change. Stella, why don’t you sit on the couch and we’ll give you a show as we do it? Do feel free to please yourself as you watch. We’ll play more seriously later. Annamarie, it sometimes is very wise, when doing groups, that the working girls please each other as often as they can, especially when they’re not supposed to do so as part of the scene. I don’t agree with situations where the sex workers take no pleasure.”

Mr. Vargas

Stella said, “The next gentleman is thinking student and supervisor, so get the appropriate uniforms. I doubt he knows the nuance of candy-stripe versus light blue true nursing student, Annamarie, so which do you think looks better?”

“Candy-stripe, definitely. If we’re going to do more of these scenes, we should get some tailoring -- maybe breakaway slits.”

“I agree. Let me get into the white uniform with blue cape. Both yours and mine, Annamarie, have high mini hemlines. A variant we might use is tan rather than white hose.

●●●

In Mr. Vargas’ room, Stella told him, “This is Ada, and her student, Annamarie. Annamarie will take your vitals.” Stella pulled a vital sign machine behind her. She wondered if the other two actually knew how to use it but realized no one really cared.

When I started to wrap the blood pressure cuff around his arm, his hand touched above my knee, and started working its way up. It reached my hemline, paused, and kept going. He had a wonderful touch. Without words, I pressed against his hand.

Ada. on the other side, gently took his hand and put the pulse oximeter over a finger. She was more facing him than had Annamarie, so his hand moved upwards, fondling between her legs. She also found his touch exciting and began to breathe faster.

Back on Annamarie’s side, his finger circled the warm bare skin above my stocking. He hooked his finger inside the stocking band. I couldn’t quite explain it, but it was hot as hell. When he unhooked the finger, I knew he’d be moving up to my pussy, and I couldn’t help giving out a gasp.

Given his fantasy was to explore and exploit without being noticed, I began to improvise like hell. “Oh, Mr. Vargas, I know that I brush against you a lot when doing these tests, but I’m sorry, I can’t help it! Does it embarrass you that it feels good for me? I must be a naughty girl, because it does!”

Ada grinned and followed along. “Yes, same sort of thing over here. You’re an incredible man, Mr. Vargas. Is it too much to ask that you explore more extensively?” He gave out a chuckle that was simultaneously naughty, happy, and lusty. Ada decided he wasn’t out to embarrass but was hesitant to admit to things. “Oh yes, Mr. Vargas. May I please you?” She pulled up on her hem, revealing the stocking and most of her leg.

I saw that and decided the fantasy had changed. Putting my hand over his exploring fingers, tenderly, I pulled them to my pantied mound. We had debated whether to go with or without panties, and I decided we had made the right choice. I slid his finger, creating a cameltoe, and pulled it up and down. That, I thought, earned me the right to moan. I heard Stella giggling and taking a seat.

He growled happily and moved a hand to Ada’s mound as well. She blew a kiss at him. He smiled, and, with his chin, pointed at the sheet tented over his groin. Understanding, she pulled down the sheet, and made an appreciative sound when his penis popped into the air.

I slid his finger under my panties and thrust at it with my hips. For whatever reason, my body wanted his finger inside me, bypassing the usual stroking and teasing.