I'm Just a Gigolo

In this chapter, Daniel is interviewed and evaluated by his female boss, Julie, first at a restaurant, then at her home. He engages in anal sex for the first time, then in an MMFF foursome and an MMF threesome with a woman undergoing her evaluation. He gets offered a contract when the evaluation if over. This chapter contains oral sex, anal sex, lesbian sex, group sex, exhibitionism and voyeurism. This is a copyrighted work of intellectual property and not to be altered, changed, edited or published anywhere. Including audio, without the authors express written permission. © Copyright 2025

I'm Just a Gigolo, Ch 2

Evaluation

I didn't think a dinner with Julie required my new tux, so I just put on a sport coat. I took the subway to Manhattan and walked into Tavern on the Green at quarter to seven. My folks always told me if I was on time, I was late, so I tended to get somewhere early and wait a few minutes. Julie arrived five minutes early herself, and she'd dressed down from the Heart Ball as well, though she still looked pretty chic in her skirt and blouse outfit.

Once more, I kissed her hand when she put it out to shake mine, and held her chair for her when the hostess seated us. It was an out of the way table without a large number of people nearby, probably necessary for any questions asked.

I pulled out a rose corsage I'd purchased and offered to pin it on her blouse.

"Yes, please."

I leaned down from behind her, letting her feel my presence, and pinned it on, with a couple of light touches to her breasts with the back of my hands and a light kiss to her neck when I finished. I then sat down, facing her.

"Do you know why you're here?" Julie asked after we'd put in our drink orders. She took out a three page list of questions and a pen to jot down my answers.

"Alberta said you ran an escort service and she thought I might make a good escort and that you'd want to evaluate me. I assume this is in the way of a job interview."

"That's true. Do you want to be an escort?"

"It sounds like I could make some money while I'm in school. I'm not sure about doing it past graduation. It might depend on how much I like it."

"Fair enough. I'd get nine months out of you at least. Did Alberta explain the job?"

"That I was to be a date for lonely women who wanted someone to attend functions with them. She said the sex was up to me, and I was never to mention sex, or that I expected any type of financial remuneration for sex if I had it."

"Listen to her. She's a lawyer and knows of what she speaks. Most of the people who hire an escort are expecting, or at least, hoping for sex. While it's true that the sex is up to you, you won't be very popular if you don't. Do you have a problem having sex with people who want it and are willing to pay for it?"

"Under most circumstances, I'd say no, but there might be some I'd be resistant to having sex with," I said. "Say if they had poor hygiene or seemed ill.

"Do you have an upper age limit that you wouldn't have sex with?"

"Do you have that many septuagenarians or older who want sex?

"They're not frequent, but they do occur. I've provided a 93 year old woman with an escort."

"I guess I'd have to be careful having sex with someone older, but I'm not necessarily opposed to having sex with one."

"How about men? Women aren't the only ones who hire male escorts."

"I'd have to pass."

"Couples?"

"How often does that occur?"

"More often than you think. Sometimes the man wants to watch. Other times he wants to participate. They want to have an MMF threesome experience, and they don't want needless romantic entanglements."

"As long as he doesn't want to participate with me, I guess. It might depend on the circumstances."

"Will you fuck bareback?"

"With proof of health. I guess I'd prefer condoms unless they're a regular and I know them well."

"Will you do oral?"

"Yes."

"Anal?"

"I've never done anal before, but I'm kind of thick. Do women often want anal?"

"Some do. They don't want their spouse to know they like it up the ass, so they'll get an escort when they're feeling the itch, or their spouse doesn't like anal because they think it's unclean, or immoral."

"Let's say I'm not morally apposed to it."

"Didn't you ever have anal with a girlfriend?"

"Like I said, I'm kind of thick. I think if they were tempted, my size threw them off."

"Are there any days you aren't available?"

"I'd prefer mostly Friday or Saturday nights. I still need to attend classes and study. I'm willing to look at things on a case by case basis, but most of the time, I think you can assume I'm out of commission Sunday through Thursday nights. Are most of the women married?"

"Married, widowed or divorced. Very few single women hire escorts, most because they don't have the money to hire one. "Do you have a problem with fucking married women?"

"I would have said yes, but I knew Alberta was married, and I had sex with her. I guess I'm open to the idea, but it would be nice if they took their rings off and didn't tell me. I might sleep easier at night." She smiled, but said nothing.

We took a pause as the waitress brought our drinks and took our orders for supper. I had a grilled chicken oriental salad, so I didn't break the bank. I had the money Alberta had paid me, but I didn't know if I was paying for this meal or not, as I wasn't an employee yet.

When the waitress left, Julie asked, "I'll want to fuck you as part of my evaluation, and you know I'm married. Will that be a problem for you?"

"Does Greg know you run an escort service?" I asked.

"He does."

"Does he know you sample the staff?"

"He does."

"Does he care if you sample us?"

"He does not, and in fact, will often watch. Would you have a problem with Greg watching you fuck me? Might it cause performance issues?"

"I don't know. I've never done it in front of an audience before."

"An honest response. Have you ever done bondage and discipline as a top or bottom?"

"I halfway understand your question, but what's a top?"

"A Dominant."

"Then a bottom is a submissive?"

"Yes."

"The answer is no. I've done neither."

"Would you be willing to spank or humiliate or otherwise Dominate a client?"

"I suppose. They would have a safe word, wouldn't they?"

"Whatever you set up between you. Would you let a woman Dominate you, including corporal punishment?"

"Maybe for an evening, but I'd probably need to know ahead of time what they expect, and how much physical punishment they intend to inflict. How often might that happen?"

"Unknown. Depends on what you allow. If you're a good bottom, tops will want to Dominate you because it's something they're not getting normally. You could end up in high demand. They do tend to tip very well, so it's something to consider. We're not charging for that, so how much depends on them and you. The Dominants will want to fuck your ass, so keep that in mind if you're opposed to a little back door action yourself."

"I've never done that either."

"I'm not surprised because of your age. Our top escorts are usually in their late twenties, up to their mid-forties. They've got experience in more things than you do, while still being handsome and fit and able to fuck for hours. Too young, they lack experience and a certain gravitas that women find appealing. Too old and there are more performance issues and bodies do tend to slip unless you work harder. I suppose I, or one of my female escorts could give you an overview of some of the more esoteric things you might run across."

We paused again as they brought our food.

"Do you have any questions for me?" Julie asked.

"How much of my date do you get?"

"Twenty-five percent."

"Do I collect the money?"

"We charge them based upon the length of time they're asking for. When we send you the information on the date, it will include their name, where and when they're to be picked up, where you're going so you know to dress appropriately, and how long they've hired you for. Any longer, they should pay more, but text us and identify how long the date lasted, and only the date, and we'll charge them. If the date ends, and you decide to have sex, don't tell us about that. They'll tip you for the excess time and attention. They're only paying us for the time you're actually on the date, where you'd otherwise be going home. They're also responsible for any meals, event tickets, and drinks associated with the dates. You're responsible for your transportation to and from, and possibly to the event, if they don't have a driver. Sometimes, a clients wants it to appear like you're paying so they don't look like they've bought you. If that's what they want, they'll slip you an envelope full of cash when you pick them up, and you'll pay as if it's your date. You can use taxis or one of the ride shares, or your own vehicle if you have one. Do you have one?"

"No. Parking is a premium I didn't want to pay for, and public transportation is easy in the city. Is that a problem?"

"Not really. Most of my staff don't use private vehicles either."

"Do I ever let my clients pick me up?"

"Only if you want them to know where you live. Most of my staff don't. They want their private time to remain private time. You shouldn't give out your phone number to them either. You want their business to come through us. They pay us, we take our cut, take out taxes and Social Security and pay you yours, so you've got a legitimate source of income."

"If I like someone who was a client and I want to see them romantically, is that a problem?"

"Not if you're not charging them for services rendered. If you're paying to date them, it's fine, but don't ever let us catch you trying to cut us out of our commission."

"That's fair. How much are you going to charge for my dates?"

"I'll set a price based upon our interactions tonight. Then, your first date will be with someone who's hired our escorts often. When you go out with her, we'll get her opinion on what we should charge, and I may update your price based upon her recommendation. That will be your price until we see how popular you are. The more clients who want you, the higher we'll set your fee. If you don't bring in or keep business, your fee will drop. Are you free tomorrow night for your first date?"

"I am."

"I'll give you the details for your date when we're done."

"Should I declare tips?"

"That's up to you, but I'd recommend staying on the right side of the government on this. They know people in your line of work get tipped, so let your conscience be your guide."

"What about gifts?"

"I'd declare any or all money or items of substantial value, but I think you can skip the smaller things."

"Alberta bought me this watch. I believe it was about $400."

"That's a small item. I was talking about cars or trips abroad, so let's say any cash gifts above and beyond tips, or items in excess of two or three thousand dollars, or anything which is registered or titled."

"People will buy me a car?"

"It can happen. One of my girls is living in a condo someone else paid for. Depends upon how good you are, and how rich they are."

"Has she got a sugar daddy?"

"He's her primary dater, about once a week, but she still goes out on dates with other people, so not a full timer. He does get to stay over at her condo, if he's in town. Saves him from paying real estate taxes on it and paying for a hotel."

"How much might you anticipate me making?"

"From us, and only working weekends? Maybe five or six hundred a week to start after our cut. More depending on any fee adjustments and the word gets out and depending on your tips, which you earn by how satisfied the customer is. Alberta raved about you, so I have high hopes."

Julie got up to use the restroom after our discussion. I stood up when she left and again when she returned, and once more helped with her chair.

"You've got the manners down pat, that's for sure. Women will love that. There's no feeling like a gentleman who you believe appreciates you. Who taught you your manners?"

"My parents."

"They did an excellent job."

"Thanks.

We both skipped dessert and the waitress brought the bill. I handed Julie enough to pay for my meal and drink plus a twenty percent tip.

"This is on me, a business expense," Julie said, handing me back my cash. "It's time to get to the physical examination."

"Where to?"

"My place is across the street," Julie said.

"Is your husband going to be there?"

"He's checking out a female applicant tonight."

"Do you ever check out the females."

"I'll be checking her out tomorrow, since she said she'll do girls too."

"Would your husband be checking me out if I said I did guys?"

"He would."

She got her card back and I helped her out of her chair and took her arm as we walked across the street. The wind was a little brisk tonight and kicking up, so I put my jacket around her shoulders. They lived in a nice swanky walk-up on the third floor. It seemed like around 2000 feet of living space, and since it was on Central Park West, had to be worth more than a few bucks. Running escorts had to be a lucrative business.

Julie took me to what appeared to be the master bedroom.

"Undress me," she said. "Take your time and make it good."

I started with my jacket, which she was still wearing, laying it over the back of a chair beside the bed. She had on a black blouse with light gray strips in it. I slowly unbuttoned the blouse, kissing her neck and shoulders as I did. It seemed her neck was a sensitive spot, because she gave a small moan as I kissed my way from her ear to her shoulder, and I filed it away. As the blouse came off, it revealed a semi-sheer white bra. Her nipples were visible, although not clear. I cupped her breasts, rubbing my thumbs over the nipples until I heard a soft whimper. I drew the blouse of her shoulders and laid it on top of my jacket. I estimated a large B or small C cup.

The bra had a front clasp which made it easy for me to unhook and reveal her breasts. You don't reach 50 years of age without gravity affecting your body to some degree. Julie was no exception, but I had to admit that she looked pretty good so far. I also suspected some cosmetic work. There was a small amount of sag to her boobs, but not much. They wouldn't pass the pencil test, but they still looked good. I licked and sucked her nipples until they were hard little nubs.

"Very nice," I said. "You look great Ms. Myers. I love your breasts. They're very soft."

"Mmm. You do that just right. You don't suck them like you're trying to draw milk, but you don't baby them either," Julie said.

As I sank down to my knees, I kissed my way down her slightly rounded stomach to the waist of her skirt, a dark gray knee length, that went with the blouse. I undid the button at her waist and drew down her zipper, the skirt dropping as I did, revealing the white, Brazilian cut, high waisted underwear and gray, nylon thigh high stockings. I had her step out of the dress, which I added to the chair, then kissed the front of her panties over her mons. I rolled down each stocking, then ran both hands down her left leg, and up her right. The skin was not as elastic as someone younger, but still smooth and shaved. What I'd done so far had gotten her aroused, and there was a small damp spot on the gusset of her dainties, and I began to smell the tart scent of her arousal.

I drew down her panty revealing a bald pussy with fairly prominent inner lips with a hint of her dew. Her clit protruded slightly from the surrounding hood, and I gave it a quick kiss and a lick before standing.

"Pretty good, Daniel." She sat on the bed. "Now take off your own clothes, and make a small show of it."

I slowly unbuttoned my shirt, doing some brief flashes of my pecs and abs as I did so, and even after it is open, turning and teasing Julie with displays of my stomach or chest before finally peeling the shirt off. I took off my belt and pretended I'm going to smack Julie with it, before tossing it to her. I did the same with my pants. Once they're unzipped, I peel back one side or the other and give her glimpses of the silk boxers I'd worn. I'm already pretty excited, and my dick is ready to pop out the hole in front. I finally pull both sides out, and my cock pokes out of the fly in front, 3/4 hard. I step out of my pants.

"Is this what you want, Julie? Do you want me to fuck you?"

"I'd love for you to fuck me," Julie said, a smile on her face. "Nice job. Lose the boxers."

I reached into the pockets of my pants and pulled out the three different condoms I had there, tossing them on the bed. One was ribbed, one glow-in-the-dark, and one was lubricated.

"Lay back and spread your legs. I want to taste you pussy. You're officially going to be the oldest person I ever had sex with, and I want to start it off with a bang."

I worked hard to give her the best pussy licking I could. I figured this is where I've started to set the price of my services. I needed Julie to believe that all of my clients would get this level of service from me, and I wasn't afraid to dip my tongue in a hot box, no matter how old they were. She got three orgasms from my tongue before she told me to fuck her hard.

"Pick your condom and put it on me," I said.

She picked the ribbed one. I thought she would. The glow-in-the-dark was a little juvenile and the lubed one fairly plain. The ribbed condom wasn't lubed, but I'd made sure her pussy was plenty wet. She got on her hands and knees, and I slowly eased my rubber clad dick into her pussy doggy style. She gasped and orgasmed as my fat prick spread her pussy lips wide.

"You do have a fat one, don't you?" Julie moaned. "I love this."

"Would you want it in your ass," I asked.

"We'll be finding out," she said.

I fucked her to two orgasms like that, then she wanted to change to a missionary position, and it was the first time I kissed her lips. I think that she didn't necessarily want to kiss, but when I gave her a good strong thrust and her mouth opened in surprise, I claimed it. After that, she was an enthusiastic partner in all of the rest of the kissing we did, never turning away if I wanted to kiss. She had two more orgasms, shivering delightfully through each one. I paused my thrusting for the first, but fucked her through the second which seemed particularly intense, and then I climaxed myself, filling my condom with my seed. We were both breathing pretty hard at this point.

Despite my orgasm, I continued to kiss and caress Julie, even fingering her to another orgasm, demonstrating I knew where her g-spot was. Her back arched as she climaxed, whimpering soft words of encouragement.

"There, there, don't stop, perfect. Oh, fuck, I'm cumming."

She was quite limp when she dropped back to the bed.

"For a young guy, you're exceptionally good at this. How did you learn to make love to a woman like that, an experienced older woman?"

"No. I paid attention to what my girlfriends seemed to like and not like. It's sort of like holding a door for me. If I take care of her, she takes care of me. They appreciated what I did for them, told me I was much better lover than the other boys my age, and I figured I was doing something right, so I kept doing it."

"Would you like a shower?"

"I do feel a little sweaty, so yes, thank you."

We took a shower together, washing each other. She was pleasantly surprised when it didn't take much to get me hard again.

"Nice recovery time. Not surprising considering your age, but good."

We dried each other off and she sent me back to the bedroom. "I have something else I need to do in here. Try to relax, but don't fall asleep. It shouldn't take more than twenty minutes."