I had a semi-regular client named Jonathan. He was in his early fifties, and kept himself fit and smelling pretty good (those things matter, trust me). His wishes were pretty vanilla – i.e., he’d hire me for a couple of hours and we would have pretty basic sex, running through most of the common positions and things that a man and woman can do to and for each other. He always enjoyed himself enormously and I liked him a lot. He often remarked that I was very good at it. As he got to know me better, he would extend the time a bit to last after his orgasm just for pillow talk. He liked my abilities as a conversationalist, and I found that gratifying. “Refined,” I think was the word he used to describe me. And “genteel.”
So perhaps it wasn’t all that surprising when Maxine told me that Jonathan wanted to talk to me about some matter that was very important to him. I couldn’t imagine what it might be… but I was happy to meet him (off the clock) at my favorite coffee shop to talk about whatever was on his mind.
Turned out it was his son that was on his mind, a lad named Josh who still lived at home. Jonathan said that the young man was a complete addict to social media and all things internet, but that he had little to do with actual people in his real life. “The kid is twenty years old,” said Jonathan, his voice trembling with some emotion. (Anger? Disappointment? Frustration?) “He lives in a lair in the basement, he has no job, no friends, no life outside his computer. And, as near as I can tell, his life there is nothing but a silly fantasy.”
“I’m no expert,” I said, “but I don’t think that’s so uncommon.”
“But this kid,” said Jonathan, “is still a virgin. At twenty.” The words came out as a sort of groan. “I lost my cherry at sixteen,” he continued, “and I have friends who were younger than that when it happened to them. And Josh is twenty and never been kissed, much less fucked.”
“You know this for a fact, Jonathan?”
“I do. The last time he was alone with a girl was at a play date with my sister’s kids.”
“Aha. How old was he then?”
“Three,” he said. “Maybe four.”
“Oh!”
“Besides, he talks to his younger sister sometimes, and she confirms it. And she, by the way, lost her virginity at fifteen, as she’s proud to tell me.”
I wanted my next question to be delicate, but couldn’t come up with a nice way to put it, so I didn’t even try. “Are you quite sure he’s even interested in women?”
“For sure. He can’t be bothered to ever turn his computer off and clear his ‘history’ page. And he sleeps like a rock all morning long. Every time I’ve checked, it’s full of visits to porn sites, all of them hetero. It’s pretty tame stuff, no real…kinks that I’ve noticed.” Here Jonathan looked a little uncomfortable in a way that made me wonder if he himself was, in fact, as vanilla I’d thought. Maybe he’d been keeping something back.
“Sooooo…” I said.
“It kills me to think he’s missing out on his best years! And he hasn’t even tried it. Serryn, I need something to bring him out of that dungeon he’s created. College didn’t do it. Sports didn’t even come close.”
“So you’re thinking…sex might?”
“I’d say it’s worth a try.”
“You want to hire me to initiate your son?”
“Is it something you’d consider?”
“Sure,” I said, “it sounds fun. You’re sure he’s not underage, Jonathan?”
He reached into his wallet and took out a driver’s license. He looked at it for a moment and sighed. “Something else he’s not using,” he said, and handed it to me. The photo showed a pasty-faced, somewhat overweight young man. The date checked out: Josh was about to celebrate his twenty-first birthday. I pointed to the date. “Are we talking a birthday party here? A present from a doting, dear old dad?”
“Something like that,” he muttered. “But we’ll keep it to the three of us: you, me, him. His mother doesn’t need to know.”
“Of course,” I said. “I’d known Jonathan for two or three years, and this was the first time he’d ever mentioned a wife…whether ex or current he didn’t say, and I certainly didn’t ask. “I’m ten years older than him,” I said. “How do you want to play it?”
“I thought about trying to set up something that seemed spontaneous,” he said, “but the kid hardly ever leaves the basement, so the chance of you guys meeting in a bar or coffee shop seems impossible to pull off. I think I’m just going to come out and explain matters to him. We’ll set you up in a nice hotel downtown, I’ll put Josh in a cab, give him a key card to your room, and have you there when he opens the door. The details of how it goes after that, I’ll leave to you.”
“Prudent,” I said. “And I won’t tell him you know me. I’ll just say you called the agency and they sent me.” Then another thought occurred to me. “What else did you find in his history…besides heterosexual porn?”
He waved his hand dismissively. “A bunch of bullshit. Dungeons and Dragons stuff. Knights in armor, fair damsels in distress. He has this character he apparently goes on and plays with, an…an…What do you call it?”
“An avatar?”
“Yeah, an avatar, and it’s this dark-haired, skinny minstrel or something called Baldric. Doesn’t look a thing like him.”
“Is Josh a musician?”
“No, he can’t play the guitar for shit. I’ve tried to teach him some Pink Floyd, I’ve tried to teach him ‘Wonder Wall.’ He’s hopeless.
But Jonathan had just given me a way in.
I am aware that I have tried to present myself in these sketches as being some uber sophisticated, jaded, been-there-done-that woman of the world…But I might just as well come out and say it, I’m actually a total, hopeless geek, possessed of many geek-like traits which perhaps I need not get into. All you need to know about how deep my geekdom goes, is this: I am a complete lover of Renaissance Faires, and have been for as long as I can remember. You’ll understand the depths of my commitment when I tell you I have not one, not two, not three, but four separate outfits: Elizabethan Noblewoman, Leather Armor-clad Woman Warrior, Saucy Country Wench. The fourth outfit is actually for very hot days and it is a sort of fairy get-up: two long scarves with nothing underneath, held strategically (more or sometimes less) in place by a big, broad leather belt.
I obviously couldn’t cop to Josh that I knew about Baldric the Minstrel, but his love of Medieval gaming – and games in general – gave me a plan. I rejected Noblewoman and Woman Warrior as being potentially too intimidating, and Scarf Fairy as being maybe a little on the nose. So Saucy Country Wench it was to be.
I was already pretty excited at the prospect of a novel experience, but the idea of getting dolled up in one of my beloved outfits made it all the sweeter.
I was pleased to learn that Jonathan had booked a room in the downtown New Standard, one of my favorite hotels in Los Angeles. On the phone he told me that he had re-thought sending Josh in a taxi, but had resolved to drive him there and deliver him in person. Josh would be arriving, he said firmly, at eight pm.
I got there early. I had a long, luxurious bath, sipped a glass or two of champagne, and took my time getting into costume. Saucy Wench outfit included a very low cut blouse with an outside corset that plumped my small tits up nicely, making them look a lot more bountiful than they were. Then I festooned the room and bathroom with candles. The L.A. New Standard wasn’t exactly a Medieval Inn, but I had given it a pretty magical aura by eight o’clock…
At precisely which moment there was a timid knock. I tousled my hair, pulled the blouse down a little lower, and opened the door. A pale, pudgy young man with a wispy little mustache and an attack of acne stood there blinking at me, blinking at the candles. I’m not sure what he thought he was seeing. I was dying to call him Baldric and do my, “Prithee, fair gentleman, well met!” but I decided to dial it back. “Hello, Josh,” I said, “I’m Serryn, and I’m very happy to meet you.”
“He was quite nervous, and clearly knew what he was there for, though precisely what his father had told him I never learned. He asked me why I was dressed that way, and that gave me an excuse to tell all about my Ren Faire fantasy of being taken by the wealthy Squire’s handsome son. I could tell that he liked that a lot.
It was pretty obvious that he wasn’t going to do anything to move matters along, so I decided that I had better. “Have you ever played strip poker?” I asked him.
“I don’t know anything about poker,” he said.
“We could play a very simple version. We each turn over a card. The person with the low card has to take something off.”
He swallowed hard, but said, “Okay.”
We sat on the big king bed and I produced a pack of cards. He really didn’t know anything about them. I had to explain the hierarchy with the face cards. To my frustration and Josh’s discomfiture, the cards didn’t like him. I had him out of his shoes, both socks, and shirt before I ever drew a low card. My corset laced from the back, so, though I didn’t really need it, I asked for some help. I could tell that his hands were shaking as he unlaced me. Facing each other again I contrived to lean toward him, knowing that my loose peasant girl blouse would sag far enough that he should have a pretty full of view of my breasts. As I dealt him a card I sneaked a glance at him and, sure enough, his gaze focused down below. I lost the next round too. “Well,” I said, “here goes.” I took the top off leaving my breasts bare for his examination. I wondered at the moment what it would be like to have watched a lot of porn without ever having had actual sex. Breasts and asses and genitals would be familiar sights in all their glorious variety, but there were bound to be surprises: the texture of a female breast which is unlike anything on earth, the scent of an aroused woman’s pussy.
