In this chapter, Dan talks about the youngest client he ever had, and her young girlfriend who he helped in another way. This chapter contains oral sex, sexual intercourse, some light anal play, masturbating, and sexual instruction and discussion. My thanks to JohnnyGalt for his help. This is a copyrighted work of intellectual property. As such, do not alter, edit, change, or publish this in any way shape of form, including audio, without the written consent of the author. Β© Copyright 2025
I'm Just a Gigolo, Ch 4
My Youngest Client
As you've probably realized by now, I didn't stop escorting women when I graduated from college. I was making real good money, just on the weekends and once I could do it full time, my income more than doubled, even though the demand on weekdays was usually less. I got some week long trips to exotic locations, cruises, trips out of town, and I had to say, no matter who I was escorting, they liked the sex I provided, and were giving me some really nice tips.
This story takes place when I was twenty-nine, so eight years after I started. I could have a 'date' almost any night I wanted one, although I did take breaks from the work from time to time. I was usually in heavy demand and my prices reflected that. I was now making almost double what I'd started at, trying to keep a balance between supply, limited to me, and demand, high.
I was spending the night with a delightful, if somewhat well padded, divorced woman of forty years of age, named Shannon. She usually hired me about once every three or four months to take the edge off.
"Yes, fuck, yes, lick me there. God, you're good with that tongue of yours. My boyfriend wouldn't know how to find my clit if I hung a sign on it. What's worse is he thinks he's God's gift to women. That's right, right there, that's perfect. Don't stop."
My face was shiny from her juices, and since she didn't want me to stop, I didn't, at least not until she'd had three more orgasms, which is when she told me she was getting too sensitive.
"Why don't you tell him what you want?" I asked, resting some between her legs while we both recovered.
"How do you tell a man who thinks he's God's gift to women, that he doesn't know a pussy from a hole in the ground?"
"Very carefully, I imagine," I laughed, "unless you want to hurt his feelings."
"I'm not sure I can hurt his feelings. I've tried to tell him what I like a couple of times, and he just keeps on doing what he wants."
"Why go out with him then?"
"He's pretty nice except in the sack. Just an oversized ego because he thinks his dick makes up for lack of quality."
"Pretty big?"
"Not as big as you are, but more than most, I guess. Do you think you could give him lessons?"
"You want me to fuck you in front of him?"
"Probably not a good idea, huh?"
"Not if he has an ego."
This conversation became prophetic in the future.
"Maybe you could fuck someone else in front of him?"
"It's a possibility, I suppose, but unless he's willing to take direction, will probably fail."
"Are you free in a month?"
"I don't know. I don't keep my calendar. Why? Want to arrange another date so soon?"
"My daughter is turning eighteen in a month. I'm pretty sure she's a virgin, and I'd like you to be her first."
"Why me?"
"Because you're the best, and I'd like her to have the very best her first time. Believe me, my first was a disaster. I wouldn't wish that on anyone."
"Don't you think if her first time is that good, all the sex she gets afterwards will be a disappointment? Shouldn't she experience some average sex instead of getting spoiled right out of the gate?"
"I suppose that could be a problem, but maybe once she knows how good it can be, she can train her subsequent lovers what to do?"
"Like you're training your boyfriend?"
She laughed. "Okay, bad example, but not all men are as obstinate as he is, and I think young men could be very trainable, as they'll do anything to get pussy. I doubt that's changed any since I was a teenager."
"Does she have a boyfriend now?"
"She does, but I'm not sure how serious she is about him."
"Maybe she'd prefer losing her virginity to him."
"I think I can convince her otherwise."
"What day are you interested in?"
"July 22, and I want you with her for two days and two nights, say from six PM on the day of her birthday until six PM on the 24th. Can I get the friends and family discount?"
I laughed. "That's up to Julie. You need to negotiate that with her. Do you want to prepay so I take care of all her expenses?"
"That would probably be best."
I sent a text to Julie asking her to reserve the days in question for a client, and if I was already reserved, see if she could change it, as this was a birthday gift, for a birthday girl. She said she'd take care of it.
"What's your daughter's name?" I asked.
"Fenix, spelled with an FE instead of like the city."
"What's she like?"
"Smart as a whip, National Honor Society, a bit of a bookworm and shy, which is probably why she's still a virgin. She wears glasses. She's taller than I am by about two inches. Very nice figure, although a little small up top. I think she's quite attractive, although I know I'm prejudiced."
"What if she doesn't want to give her virginity to me?"
"I'm sure you can convince her. You're very persuasive with that tongue of yours, which, by the way, I'm desperately in need of again. Get me warmed up some more, then shove that big cock of yours where I need it."
I resumed licking her pussy, giving her another orgasm in the process, before she mounted me in a cowgirl and rode me to three more. She fell asleep in my arms, feeling extremely satisfied. I got a huge tip the next morning.
******
July 22 was a Wednesday this year, so not a real high demand day, but I did have a prior date scheduled for the 23rd which Julie had to move with the promise of a 20% discount. Luckily, it wasn't anything that couldn't be moved because it was only a dinner date.
Shannon didn't want me showing up at her house because her boyfriend would be there, and I was eleven years older than her daughter. Having to explain why Fenix was dating someone much older, and why she would be safe with me, was more than she wanted to explain to the boyfriend, Brad, so I was to pick Fenix up from a friend's house, where she was supposedly celebrating the birthday with her friend, on a two day sleepover.
I was successful enough that I'd bought a very nice car, so I didn't have any problem picking Fenix up. The date consisted of me taking Fenix to a very nice dinner at the Ritz, with a hotel room at the same place, charged to Shannon's credit card. I could charge the meals to my room, and all would be paid for.
The friend lived in a brownstone in Brooklyn. I'd purchased a corsage and seen a picture of Fenix, so I would know what she looked like, so when the friend opened the door, I knew it wasn't her. It was the girlfriend, a slightly plump girl named Svetlana, or Lana for short. She invited me in, and I waited at the door while Lana got Fenix.
When Fenix showed up, she was dressed in jeans and a tee shirt, not at all what she should be wearing to the Ritz on her birthday. She was 5-8, 5-11 with her three inch heels, slim, brown hair worn shoulder length, brown eyes, nice smile, and of course, the glasses.