I'm Just a Gigolo Ch. 02

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."

Rather than lie on the bed, I walked around the room, looking at the art on the walls, a picture of her and her husband on a beach somewhere, maybe ten years ago. It was a happy picture, with both of them laughing, and having what appeared to be a good time. I thought about the fact I'd just fucked Greg's wife, and he was doing the same thing with another woman right now. Did they still love each other? Would they have another picture like this one in the future, laughing and happy?

I didn't hear Julie crossing the carpet and I was a little startled when she put her arms around me and kissed my shoulder blade.

"Are you and Greg happy?" I asked. "Do you still take vacations like this one?"

"We're very happy," Julie said. "Just because we fuck other people, doesn't mean we don't love each other. We don't equate sex with love, nor do we think that just one other person can give us all we desire in the world, so we feel free to be with others, but we always come back to each other, ready to face the next challenge."

"Do you have children?"

"I couldn't have any. Greg has one from a previous relationship. He's twenty-five now, out in California, with his mother, working in the movie business as a cameraman and boom operator."

"Is this your bedroom, together?"

"No. We have our own. This is our testing bedroom. We both use it, but not with each other."

"Where's Greg tonight?"

"At a hotel. We flipped a coin, and he lost."

I turned to face her and we kissed again. She eagerly accepted the kiss, no hesitation.

"You seemed to be reluctant to kiss earlier. Is that because of your marriage?" I asked.

She laughed. "Oh, wise one. Yes, it's because of Greg. I don't often kiss the staff, but I have to admit, I'm enjoying it. You're a good kisser, and it does enhance the sex."

"Would he be upset if he found out."

"Surprised, but not upset. That's petty in the whole scheme of things." She reached down and grabbed hold of my cock. "Ready for another round?"

I'd deflated while waiting, but it wouldn't take much to get me going again.

"I'll be good with a little encouragement. You want to taste my cock?"

"Sorry, that's where I do draw the line for Greg. Other men's dicks don't go into my mouth. Pussy and ass, yes, Mouth no. I'll get you up, don't worry."

She got some lube from the nightstand and lubed up my cock, giving me a very good hand job, her hands nice and slick. When she got me hard, Julie told me to lie down on the bed. She put the lubricated condom on my cock and then added more lube to my cock and her butt.

"Since you are a butt buster, I suggest you let the women who want it, ride you in a woman superior position. They can go as fast and easy as they want. Let them, don't thrust until they start sliding up and down on your dick. They'll let you know when they're ready for you to take over."

"Got it."

She smiled. "l bet you do."

Julie slowly lowered herself over my prick. I was surprised she went as fast as she did, but within a half minute, she was resting on my groin. I was having my first anal sex. It was very tight, and I could feel every time Julie clenched, almost as if she was trying to force me out. She just sat there for a minute or two, adjusting to my size. Finally, she began fucking herself and bouncing up and down. I remained still for a while, waiting for her to say something.

"You can start thrusting if you need to," she said.

"I'll cum faster if I do."

"How much faster?"

"Say fifteen minutes instead of twenty."

"That's fine, thrust."

I started to thrust. Actual thrusting usually made me cum faster even if it was the same speed. It's like my body needed to feel those muscles tightening to recognize I was having sex and prime the pump. About as I expected for the second time this evening, I lasted around fifteen minutes. Julie seemed to love her anal fucking, cumming three times before I did. She collapsed down on me when I climaxed, breathing hard and finally kissing me again, having gotten over her initial reluctance.

"You were great, stud. Women are going to love your dick."

My cock was shrinking and I pulled out of her posterior. I was surprised the condom wasn't coated in fecal matter, since I'd had it shoved well up her butthole.

"Why isn't my condom dirtier?" I asked, as I pulled it off to throw away.

"I took a couple enemas just before our sex, otherwise it would have been dirtier. If I know I'm having anal, it's my normal routine. It's much nicer. I do it often enough it doesn't even take that long."

"Is your evaluation done? Should I leave?"

"Spend the night with me. I'd like to see how things go tonight and in the morning."

"Okay, just let me go early enough to get ready for my date tomorrow?"

"Don't worry, I'll take care of you."

******

We went to bed and cozied up to each other. We kissed and cuddled a bit, and then we fell asleep, our bodies entwined. I woke up with a woody, and after licking Julie awake, we fucked again, using the glow-in-the-dark condom, my last one. We fucked in a number of different positions, me shifting when Julie told me to try something different. We were in a modified missionary position for the second time, and I was going for the kill. I had her legs resting over my elbows, opening her up good for some serious fucking. I was pumping her pretty fast and deep, and she was moaning and calling out my name and cumming hard. I was kissing her to keep the noise down a little.

There was a knock on the door to the bedroom and I looked up and Greg was standing there, a bemused smile on his face. I almost stopped fucking his wife, then figured, 'what the hell' and kept right on nailing her good.

"What's the verdict?" Greg asked.

"He's going to make us a ton of money, honey. How did yours do?"

"She shows promise, but she could use some seasoning. Her cock sucking skills are marginal. Should we use Danny Boy to show her what to do and practice on?"

"He definitely knows what the hell he's doing. His cock might be a little too big for her to handle right out of the gate, but if she can get him down, she won't have many problems with most men."

"Today?"

"I've got him a date with Andrea for tonight. It might have to wait a week."

Greg chuckled and left us alone.

I had to admit it was odd fucking a woman in front of her husband. Last week, I couldn't have imagined any such thing. Today? I wasn't sure what to think about today. Life had a way of turning things upside down when you least expected it, and I hadn't expected anything like the last week.

We finished up when I orgasmed, with me continuing just long enough to give Julie the last of her four. Although the rubber kept things pretty clean in Julie's pussy, I still cleaned up a little down there before getting up and tossing my condom in the trash.

We took another shower together, than she handed me a robe and said, "Put this on. Greg's got breakfast started, and we're going to eat."

I was a little surprised that Julie wanted to parade me out in front of her husband, but I did as I was told. As far as I knew, I was still being evaluated.

Greg had some scrambled eggs, fried potatoes and bacon waiting for us when we joined him in the kitchen.

He told me to sit, then set some food down in front of me.

"Are you hungry?" Greg asked.

"Starving." I attacked my food to prove it.

"My wife tuckered you out last night?"

"She did pretty good," I said. I was answering him between bites.

"You have any medical issues we need to know about?"

"None I know of."

"When's the last time you had bareback sex?"

"With Alberta last weekend."

"She usually insists on condoms."

"Given my age and that I always used a condom with my last girlfriend and hadn't fucked anyone since my pre-school physical, I guess she felt safe, because I only used one the first time we had sex. It was all I had on me."

"How are his oral skills?" Greg asked Julie.

"Better than yours," she replied,

"Really?"

"Better than anyone his age I ever met before," Julie confirmed.`

"You do any anal with him?"

"Last night."

"How did that go?"

"He's got a fat prick that takes some getting used to, but it feels amazing in my ass."

"Is he willing to do men?"

"No," Julie answered for me. "He was pretty adamant."

"Threesomes?"

"As long as it doesn't involve him taking a cock, he was okay with it."

"What are you thinking of charging for his services?"

"Max rate, and maybe higher based upon what Andrea says tonight."

"You know he'll be the youngest max escort we have?"

"And worth every penny of it."

"Damn, Julie."

"What can I say, Greg? If you don't stay on your game, I might be sampling our new employee on a regular basis. What time is Cynthia coming over?"

"Around noon."

"Maybe we can take a look at the two of them together. Cynthia will love his dick."

Greg said, "Stand up, Danny Boy. Let's have a look at your equipment."

I stood up and opened my robe. Greg didn't get close, just took a look at what I was packing. I gave him about fifteen seconds to look, then closed my robe and sat down.

"Are you willing to have regular medical check ups?" Greg asked.

"What do you consider regular?" I asked.

"Monthly."

"Do you pay for them, or do I?"

"Doesn't the school cover your health care?"

"I have a co-pay of $20 and a deductible of $2000. It's not free. I'm not even sure if it includes regular visits to check for STD's. They might tell me to wear a damn condom and quit taking risks. Don't most of your clients want to be protected from potential diseases by having their escorts use rubbers? I certainly would want to use them most of the time unless I knew someone was clean."

"Some women like to feel a man cum inside of them. A few times we've supplied an escort to get a woman pregnant. Either a single woman wanting a baby but not wanting a husband to have one, a lesbian couple, or in a couple of cases, an infertile husband paying for one of our escorts to breed his wife. I suppose we could cover any co-pays or deductibles when we needed you to be checked," Julie said.

"Hopefully, the escort doesn't have to pay child support?" I asked.

"No, all parties sign contracts specifying the sperm donor isn't responsible for any child support."

"If we're signing contracts, are we admitting to sex for money?" I asked.

"You're admitting to providing a child for money, not the same thing as prostitution."

I thought about that, having a child I might not ever know running around somewhere. I didn't know how I felt about that. Not sure I knew how I felt about much of this so far. It was happening pretty fast. I loved the sex, and I'd love to get paid for it, but some of the other things they were asking had surprised me, and I hadn't had time to really consider the ramifications of what it might mean in the long run.

Greg disturbed my musings by saying, "We're ready to extend a job offer. Do you want to be an escort?"

"I can quit any time, don't have to accept dates if I'm otherwise engaged or busy with school, and don't have to have sex if I don't want to?" I confirmed.

"Yes," Greg said.

"Yeah, I'll do it," I said.

If I tried it and didn't like it, I'd quit. Greg left the room and came back five minutes later with a contract. He handed it to me.

"Read this over carefully and then sign it," he said. It was five pages long, although it looked legible and easy to digest.

I knew better than to sign anything without going over it with a fine tooth comb, including any small print. There was no small print. Essentially, I was agreeing that I was allowing Greg and Julie, as Elite Escorts, to be my exclusive agent for arranging dates, and that they were to be paid twenty-five percent for making those arrangements. It didn't say anything about sex with other people, except that sex was not included in the dating arrangements and that any sex which occurred after a date would be a decision between the parties involved. It outlined the rules of the date, such as my providing my own transportation to and from a date, that other costs were the responsibility of the client.

There was some legalese that was fairly easy to interpret. On the whole, it was pretty straightforward, and I didn't have a problem signing it. The last page was separate from the contract and was a scale of what I was to be paid, and it was pretty much what Alberta had mentioned to me. Two hundred dollars per hour, one thousand per night, three thousand for a weekend, and ten thousand a week. I didn't see me getting paid for a week unless it was winter or spring breaks or I'd graduated. Greg told me the last page was a separate document and not part of the contract, so that they could alter my fees as necessary without affecting the balance of the paperwork. I signed that one as well, then Greg signed it.

Greg and Julie both shook my hand and said, "Welcome to Elite Escorts."

Julie added, "Let's talk about tonight's date. Andrea hires one of our escorts about once or twice a week. She's 36, divorced, and very wealthy. She's a little heavy, but not fat by any means. I told her I was sending someone new tonight, and I'd appreciate some feedback from her. She's going to take you to a Broadway show. I don't know which one. You'll be meeting her at seven, an hour before the show is due to start. Her home is within walking distance of here, a couple of blocks on this street. The clothes you wore last night are fine, although I'd like you to wear a tie. Greg can let you borrow one of his. She'll have her driver bring you to the play and back to her home. You'll chat and entertain her before and after the play and during the intermissions. Feel free to drink a couple of drinks if she offers.

"She's paying for five hours, which lasts until midnight. No sex until the date is over. Post date, she likes sex. If you do for her what you did for me, you should do fine. She'll tell you what she wants. Nothing too kinky, it's pretty straightforward. If you ring her bell a couple of times, she's an excellent tipper."

Seven to one, five hours, a thousand bucks, essentially the same as she'd pay for an overnighter, so I guessed less than five hours was typical, or why not pay for the night, but if I couldn't have sex with her until the date was over, she'd want it over before the night was gone.

"Is the tip dependent on the number of orgasms she has?" I asked.

"Not necessarily, at least to my knowledge," Julie said, "maybe it depends on the quality rather than the quantity."

"Do you want me to report to you the amount of the tip?"

"No," Greg said, "as it makes us seem complicit in the sex that follows. You just tell us when the date ended, and everything past that is on your own time."

"Does someone get a refund if the date doesn't last as long as they hired me for?"

"If it's a whole hour less, but even part of an hour is charged," Julie said.

"Is it a coincidence that five hours is the same price as an overnighter?" I continued.

"Not really. If it's going to be at least five, it should be for the night, because we know you'll be fucking them anyway, if all goes according to plan," Greg said. "Might as well point out to the customer the benefit by going by the night instead of paying an hourly rate, assuming you are going to sleep at some point during the night. The nightly rate goes from six PM to six AM the next morning."

"If someone pays for an overnight, does that mean the sex can't start until the date if over at six AM."

"The sex on an overnight can start whenever you and the client decide it can start. It's only the hourly rates that limits the sex to start after the date."

"And the weekend rate is more than two nights rate because?" I asked.

"Because you could have worked between the two nightly rates and made more money. That's reflected in it being three thousand, but they actually get more than two nights and five hours, so it's still a better deal for the client," Greg explained.

"When would a weekend date typically start and end?"

"Six PM Friday to six PM on Sunday. If you have to leave earlier, let the client know when you have to leave on Sunday."

"Okay. I guess that answers the questions I had. I might have more."

Julie took me to Greg's closet and picked out a tie to match what I'd worn, plus she washed my shirt, underwear and socks, since I didn't have a change of clothes with me. By the time that was all done, Cynthia had arrived. She was taking off her clothes at Greg's behest when Julie and I walked in after changing the sheets on the bed I'd slept in and had sex on last night. All I still wore was the robe I'd been given when I woke up.

Cynthia was a lovely young woman. I'd estimate that she was only a couple of years older than me, so early to mid twenties, a redhead, slim and elfin, perhaps B cup breasts, closely trimmed thatch proving that she didn't dye her hair. She seemed a little embarrassed by us walking in while she was disrobing. Greg introduced us to each other.

"Cynthia Pritchard, you've met my wife, Julie, and this other young man is Daniel Bradford, who has just been hired as a male escort. As you know, we're going to test your willingness to have sex with a woman and engage in group sex. Why don't you go with Julie and get started with her. We'll join you in around ten minutes or so for the group sex."

"Yes, Greg," she said.

Julie and Cynthia disappeared into the bedroom with the clean sheets. Greg and I gave them ten minutes or so before following them. Julie was lying legs spread on the bed with Cynthia lying between them, licking her pussy. I'd been half hard in anticipation, but when I saw them, it was instant erection. My cock was tenting the front of the robe and was as hard as I could remember. Greg removed his clothes.

I would estimate that Greg was above average, but still shorter than I was and less thick. He got on the bed with the two women and told Cynthia to keep licking but to raise her hips. When she did, Greg tested the dampness of her pussy. It seemed somewhat dry to me. Greg must have agreed with my assessment. He went into the nightstand drawer and removed a couple of condoms and some lube.

"Put on the rubber," Greg said, tossing one to me, "and use the lube to get Cynthia more prepared for your cock. When you've prepared, make a nice slow penetration of her pussy."

I tossed my robe on a chair and rolled the condom over my dick, adding lube to it, then climbing onto the bed behind Cynthia, and added some lube to her pussy. I spread her legs a little more so I could kneel behind her, then slowly eased my way into her pussy. I was pleased when she orgasmed as soon as my cock head rubbed over her g-spot on my way to balls deep.

Cynthia liked my fucking enough that Julie had to keep reminding her to lick her. We fucked like that for five minutes, then Greg stopped the action and told the two women to get into a sixty-nine while lying on their sides. It seemed to me that Julie was the better pussy pleaser, just from observation. Greg told me to get behind Cynthia and start fucking her some more, while he got behind Julie without a condom on and entered her. I could feel Julie moving between Cynthia's pussy and my balls, and Cynthia was told to do the same thing.

Cynthia was climaxing frequently with the dual stimulation of my dick and Julie's tongue, so she seemed to be enjoying herself. Before I orgasmed, Greg stopped the proceedings and had Cynthia mount my cock while I laid on my back. He told both of us to hold still for a moment. I could feel his fingers start to open up Cynthia's ass right beside my dick, then lube started running down onto my balls as he put some on her back channel. Greg put on a condom and told both of us to spread our legs further apart and for me to spread Cynthia's ass cheeks, so he could get between them for an anal penetration. I saw him maneuver himself between our legs, and then his hairy balls were dangling onto mine as he slowly entered Cynthia's ass.

About halfway in, I felt his cock rubbing against mine as he got deeper with only the thinnest of her membranes between us. Cynthia was panting and breathing harder as Greg's cock entered her bum. When he was fully seated, he told me to start fucking her, and I did, although slowly, because I knew she was stuffed full with a lot of cock right now. I admit it felt weird feeling Greg's cock so close to mine, and his hairy sack flopping over mine.

I could tell that Cynthia was uncomfortable to start, but as she got used to it, began to relax and really get into her double penetration. She started to orgasm frequently as we both continued pumping in and out of her two holes. We fucked like that until I gasped that I was cumming. I felt Greg's cock swell and cum shortly after I did, and Cynthia climaxed again while our cocks continued thrusting as we emptied our balls.

We disentangled ourselves and Greg and I tossed our condoms in the trash can. Both of Cynthia's fuck holes were a little distended from her double penetration, but her anus gradually started to close as I watched.

Julie told us to take a shower together and told Cynthia she wanted her to shave my cock and balls smooth in the shower. She could leave a little soul patch over my cock.

"You're a little too hairy, Daniel," Julie said. "Plus, if you shave, your cock will look even bigger."

She followed us into the bathroom so she could give Cynthia a new razor and some shave gel.

I enjoyed soaping and washing Cynthia. She really was a lovely girl. While she worked on my pubes, I asked her why she was becoming an escort.

"I started dating my boyfriend when I was in the tenth grade and he was a senior. I continued dating him after he graduated and started college at NYU. We got married after I graduated from high school. He had a scholarship and I helped support us by working as a waitress until he graduated. He got a good job so I could quit work, although we were living modestly. We were saving for our first home so we could start a family. Then, seven months ago, he was in a bad car accident and when he finally recovered, he was a paraplegic and he'd lost some cognitive function. He couldn't work anymore. I got a job as a waitress, but even working in a nicer restaurant where I could make good tips, we were burning through our savings.

"While Jimmy's insurance pays for half of the nursing costs when a nurse comes in three days a week, it's expensive. Jimmy told me to divorce him and Medicaid would pay for his treatment. I was crying in the restaurant on the day Jimmy told me to leave him. Greg saw me crying and asked what the problem was. I told him what was happening and said I didn't want to divorce Jimmy because I promised him I'd be with him for better or worse, but we were going broke, and I thought I'd have to.

"Greg told me he had an escort service and I could make better money as an escort than I ever could as a waitress, especially if I was willing to have sex. I thought about it for a week, then decided it was either that or get a divorce. I decided to become an escort and called him back and said I was ready to do it. I don't want to divorce Jimmy. I still love him, even if he is crippled. Jimmy can't get an erection anymore, so it has that benefit as well. I have missed having sex since the accident."

"Does Jimmy know that you're embarking on a new career?"

"No, I just told him I was getting a different job that paid better, so we didn't have to get a divorce. He was happy that I wasn't leaving him, so I left it at that. The accident killed some of his curiosity. He doesn't ask a lot of questions anymore."

"How many men have you had sex with, in addition to Jimmy?"

"Greg was my second. You were my third."

"Had you ever had anal sex before?"

"Jimmy and I were experimental, so yeah. I always enjoyed it, so that didn't bother me. We weren't experimental enough to bring a third person into our bed, so the group sex was new, but I enjoyed it."

"What did you do for sex before taking the new job?"

"Jimmy does a great job at oral, and in fact, he's gotten better at it since the accident, and I used a dildo when I wanted something inside of me."

Cynthia finished up my pubes, then we both rinsed off again before getting out and drying off. Julie advised Cynthia she needed to get better at oral sex with women and wouldn't get paid as much for them as she would for men. She advised Cynthia to watch some lesbian porn and pussy licking how-to videos on YouTube and see her again in a week for further evaluation.

"Dan is a real good pussy licker, so if he's got some spare time this week, you might want to take a lesson from him. That might help a lot."

I told Cynthia I could probably spend a couple hours with her on Thursday because it was a slow class day, so we made a date for Thursday afternoon at two PM. She left, and Julie and Greg fed me supper and Greg gave me six condoms.

"Carry six around at all times," he said. "You never know when you'll need them. Something else you might want to start doing is keeping track of who you date and what they like and don't like. It will be a good refresher to look at your notes if you ever have another date with them."

I was given Andrea's address and sent on my way for my first paying job, not including Alberta who hadn't really been a customer, even though she'd paid me.

So far, before I'd even started work, I've had anal sex, group sex, both MMFF and MMF, and had sex with the oldest person I've ever had sex with, plus had my gonads shaved by another person.

Next up, my first job as a gigolo, Andrea.

******