Virgin Gigolo

It was early in the morning, just a few days after Helen's party, and a day or so after meeting Martha, when my phone rang. I didn't recognize the number, which meant it wasn't anyone that I'd talked with before as I always saved numbers and names for when I got another call.

It was Melissa, the "Lingerie and More" Party hostess from Helen's "hen party." She asked if I would mind coming over to her place so we could talk. Just hearing her on the phone immediately reminded me of my first impression of her from the day of the party, a gorgeous hottie. With my cock already rising, I at first assumed she was imdicating she wanted to hire me. When I asked what she had in mind, she said she had a job opportunity but assured me it wasn't quite what I was thinking. She said she wanted to talk business but said she'd explain when I came over. I didn't have anything until that evening, so I agreed to meet her. She gave me her address.

~

"You were quite good the other day. Not many men can do what you did." The compliment caught me by surprise. What man

wouldn't

dream of being the center of attention at a hen party, having his cock sucked by almost every woman there?

"What's that?" I asked, unsure about what I'd done that was so memorable.

"Have an erection just about the whole time, letting multiple women play with you and suck you and not cum? Most men don't last that long and can't stay hard that long."

"Thank you... I think?" I laughed. It was silent for a moment.

"Listen, Brent," she said, letting me know she was getting down to the purpose of this call. I talked a bit about you with Helen. I take it you are... providing services... to multiple women around town?"

This was unusual. I had expected that she might be inquiring about my services, but I hadn't expected her to be asking about, or letting me know that she knew about, other customers. It was something that Mary had recommended that I never do and, so far, I'd always managed to skirt the issue. Nobody else had specifically approached it like this. I was immediately a bit wary, what

exactly

did she want?

"I have a 'Tree, Yard, and Other Services' company..."

"Oh Fuck, Brent. Don't give me that. You and I both know the "Tree and Yard" is to make it look different, but let's be honest. My sexy parties are a sideline, they get me in the door for other things. I fuck men for money, you fuck women for money. Right?" I didn't say anything at her brashness, not really having contemplated that she sold sex as well as sex toys. Her tone softened when she spoke again. "I understand, believe me. I was in college myself, broke and hungry. A friend turned me on to escorting and I found I could make a lot more selling sex than I ever dreamed, and then when I graduated, I was offered "good jobs" that were a large cut in pay from what I was already making. I found that I could make more with my body than with my mind. I've got an MBA, but I've been an escort, a call girl, whatever you want to call it, for years. You're doing the same thing, right?"

"Why are you asking?" I cagily asked, neither admitting nor denying anything.

"I think we need to work together."

She let that sink in for a moment and then continued. "The lingerie and toy business are just the start; like I said, that's what gets advertised and gets us in the door. But I also have a lot of inquiries for all kinds of "parties" and most are just like the other day -- what they really want is a naked body to ogle and play with and most of the time, fuck. The men want a woman, and the women want a man. Sometimes both. When they want both, most of the time what they want is a sex show -- they want to see us fuck."

For the next 20 minutes, she gave me the third degree, all while selling herself and, I later realized, convincing me I should throw my lot in with her. She told me of getting requests to perform for bachelor and bachelorette parties, hen parties, stag parties, retirement parties, birthday parties, divorce parties -- more parties than I'd ever thought of, that might include some sexual activity. She told me about how much she charged, and how anything I participated in we would share, and that anything she threw my way, she took a small cut, but that she had no desire to cut into my business. We discussed sexual safety, the use of condoms, as well as the dangers of some sexual practices.

What she said made a lot of sense.

"So how many women have you made love to?" she asked after we'd gotten away from financial discussions. I interpreted her question originally as to how many women had I had sex with, but then remembered Mary clearly spelling out there was a difference.

"I've never

made love

with a woman," I stated, "but if you want to know how many I've had sex with -- that's a different question.

She nodded. "An important distinction. I'm glad you know it. Besides your first, what about the other women you've had sex with? Are any of them older?"

"They're

all

older."

"What was the oldest?"

"I think she's 62."

"So, you've got no problem with post-menopausal women? You know about lubes?"

I nodded. "Yeah, Mary taught me a lot about everything." I didn't even realize I'd said her name.

"What about anal? Have you done that?"

I nodded my head, "Once." I didn't mention that it had been just days before.

"You stay in the business, you will -- more. Many women really like it. You'd be surprised how many women, especially divorcees, want me to fuck them in the ass with a strap-on, or more likely, they want to do it to me. A lot of times that has something to do with their divorce: she wanted something, and he didn't, or he wanted something, and she didn't. What about condoms? Do you use them?"

"All the time, all except Mary. She said that if I ever had sex with someone else without a condom, we'd start using them too, but as long as I used condoms everywhere else, we didn't have to." She didn't say anything for a moment.

"Mary? She's your first? Is that the 62-year-old?"

"Oh, shit. I wasn't supposed to say her name. Well, both. She seduced me, bought me, and taught me everything."

"What about men? Have you ever given a blow job?"

I gulped. "I'm really not into men."

She nodded, somehow realizing that I'd hidden something in the answer. "But you

have

sucked a cock?" I shook my head no. She heard what I said but somehow knew that wasn't the whole story. "A man sucked yours, is that it?" I ended up telling her about what I thought was my somewhat threesome with Paul and Lindsey without using their names.

"Not unusual. A lot of men appear dominant in public with a submissive woman who is actually the dominant one behind closed doors, and the men like being submissive. If you keep up with them, eventually she's going to want you to suck his cock. Other women will too; something about seeing another man sucking

their

man that gives them a thrill. Have you ever tasted your cum?" I nodded. "Good. That's a start. Most cum tastes similar, but just like a woman you'll get used to sucking cocks when you're asked. What about anal? What if they want to fuck your ass?"

"I don't think so..." I said, shaking my head no, knowing what I really meant was

no way in hell

.

"Understood, I've never been a fan of it myself, but I will upon occasion. It's part of the job. There was barely a pause between topics. "Just the one threesome?" I nodded; she shook her head. "You'll have more, that's a really big fantasy there. A lot of men like the idea of sharing their lady with a third. I've been in... maybe a dozen threesomes? Almost always with a wife or significant other that wants to see their man fuck someone else, or they're bi and want to share him with a woman. I've been the third with two women but never with two men, at least not yet."

Neither of us said anything for a couple of moments. I don't know what she was thinking, I was digesting all the questions that she'd asked. I don't know exactly when I realized that the questions were more like a job interview than an inquiry into my business. "Ok," she said, obviously finished, "You'll do. Are you in?"

"What?" I had to reply, having been left behind in her quick shift. "In what?"

"In business," she said, sticking out her hand. "There are no written contracts in this business; we work with handshakes. Either you're reliable and trustworthy or you're not in the business."

I didn't immediately raise my hand, thinking about it. "I'm starting college in January."

"At the U?" I nodded.

"Good. I get a lot of clients near the area. You'll enjoy that -- those co-eds seem to have some of the raunchiest parties, everyone trying to one-up everyone else. Some of the professors, too. I think they get into wild stuff when they're students and seem to just keep it up. I think it's something about academia that does it to them.

I nodded my head, and considered it momentarily; no other drawbacks coming to my mind. "Ok. I'm in," I said, sticking my hand out, to her. "When do we start?"

"Tomorrow night."

"Really?"

She nodded her head. "Last chance," she said, picking up her phone, "Once I make this call, we're committed." I nodded, she dipped her head in acknowledgement and pulled up a number. "Hey Stephanie, Melissa... Yeah, I did... just what you asked... Oh yeah, he's

really

good... Uh-huh," she giggled, "uh-huh... No, what I quoted was for two grand for one of us, either me or him... yes, I know, but that's not what was said... Ok, I tell you what, three grand for the both of us, and he'll fuck Natalie, either in her room or right there with you guys, you make the call... Yes, that's the plan, we'll fuck for at least half an hour while you guys watch and then he'll entertain Natalie alone... oh of course, as long as Natalie and I don't wear him out," she giggled, looking over at me, "but this young man is known for his stamina... yes, either of us. The three grand includes both of us together, we'll do a show and he'll fuck Natalie. Normally he gets $500 for two hours, but since we're already there, if anyone wants to do either of us, then it's $250 more each time after that..." She looked over at me, asking with her eyes that what she was negotiating was OK. I nodded. "Oh you think so?" she giggled again, "my experience in these is that probably one of your sisters is more than willing to let you, but if you want your first woman experience to be with me, I'll be more than happy to teach you what I like... Ok, 9 pm, I've already got the address. See you tomorrow. We'll text you when we're coming up to the door."

She hung up the phone and looked at me. "So, I think you heard it all. You and I are going to put on a fuck show, for at least half an hour, and then you're going to "seduce" the bride, Natalie. At least she's going to make it look that way. Natalie's never been with a stranger, never been with anyone except her boyfriends, and never done it in front of anyone else. I asked the question, when Stephanie first got in contact with me, about what she, and they, were up for. Normally with two of us, it's two thousand each, but since I sort of had an arrangement, I modified it. We'll split it, I know I told you two grand including a fuck, so for this one I'll take a thousand and you get the two thousand."

I shook my head. "No, that's not fair. You were going to entertain for two grand, and now that there's two of us you're going to take half as much? I'll split it with you."

Melissa just looked at me. "Wow, I couldn't have hoped for any better response. This business is all about us taking care of each other. So, any customers of yours are yours, anything that comes through me, we'll split. And, speaking of splitting things, I keep it all upfront so we both know what's happening. When I go out alone, I get the two grand and any extras are all mine. If it's just a lingerie party, I take everything, and when they want a male model, if you go along, we'll split the booking and I'll share 25% of the profits. Since there are actual goods to be bought and sold, it's not all profit, so not as much as what you might think you'd make, but I'll open those books and let you see what we actually made.

When I set it up so you or any of the others go out alone, $500 goes to me, $1500 goes to you, and the extras are always all yours. You've been doing this making money for school?" she asked, changing subjects again at lightning speed, "and instead you're finding you've suddenly got lots of money." I nodded. "You need to be putting money away long term. Spend it all now and it's all gone, put even a fraction away, and it will continue to grow." She looked at me, quiet for a moment, sizing me up.

"OK, bucko," Melissa said as if she read my mind, "what's your big fantasy? A hot car?" I looked up and sheepishly nodded. "Ok, look, I did learn a thing or two getting an MBA, and the reality is what you've always heard -- you can have your cake, or you can eat your cake, but you can't have

and

eat your cake. This profession won't last you forever, and if you really tried to do a gig every day, you'd kill yourself in a year. But still, there's a lot of money that you don't want to be blowing up your nose. Is coke your drug of choice?"

"Cocaine?" I said, aghast, shaking my head no. "I don't do drugs."

"None? But you smoke weed, right?"

"No."

"Alcohol?" I shook my head no. "What

do

you do?"

I thought about it for a moment and said, "Sex?" She laughed.

"Isn't that the truth? Ok, so you're not blowing it up your nose, you're not drinking it, so you're going to be having all kinds of money. First, I'm going to suggest you live frugally; pretend you don't have a lot of money, even if it seems you do. If you haven't got a good excuse for having money, it

will

draw attention. Give it at least two years before you start spending more money. Put it away now and you'll be able to retire by the time you're 30. Put it up your nose or into hot cars and one day soon you

will

be broke. I'm going to suggest that you put

at least

25% of everything into long-term investments. It's just like they say about lawyers, a lawyer should never represent themselves. I've got an MBA, but I'm not investment adviser. I've got a broker who knows how to handle it and can work with cash and is doing a fantastic job for me. If you've got an investment advisor, you don't need me to introduce you but, if not, I will." I nodded.

"Second, you've got a business, so you're keeping books for your... tree trimming, is it?" I just nodded. "Good. Gotta keep the government happy. Lots of money going into an account and they're not getting their share and the IRS comes knocking. Nobody cares that you're

really

selling your dick to horny women as long as the IRS is getting a cut. Have you got a CPA? They'll know what you can or can't use as a business expense, and you'll want to keep your nose clean. If not, I can give a recommendation. Do you have a car?" she asked, again switching gears at lightning speed. I shook my head no. "Fuck! How are you getting around?"

"Close to home I ride a bike, I've been doing that since junior high school. If I'm going where busses go, I take public transit, and if it's the weekend or evenings I can borrow my mom's car. And besides, riding a bike gives me a workout."

"Oh my God, you are

such

a baby. I guess that explains the hard body, eh?" She laughed, "A hard body with a magnificent cock, if I do say so myself. And what would your mother say if she knew you were taking her car to go fuck her friends?" She giggled. "OK, so you're going to need a car, soon, if you go to the U. Stay away from the chick magnets, they don't really work, anyway. Girls see a guy in a flashy car, and they think he's probably some dick who's making up with money for what he doesn't have in his pants. BMWs and fire engine red are for pimps. You want something newer so it's not breaking down, and when we go to our appointments it's important that we're there on time. But nothing brand new and nothing too flashy; no jacked-up four-wheel-drive truck as those things will stick out and draw attention. You don't want to draw attention to yourself; the whole point is to blend in. When you leave... a client... you want them with a smile on their face and other people to

not

remember you or what you drove up in. Just something somewhat modest. Have you got enough saved to do that?" I nodded.

"OK, so tomorrow night," she said, changing gears again, "do you think you can fuck me for show?"

"For show?" I repeated, "not for real? How do we do that?"

"Oh, it's real enough, you'll get to fuck me, but we need to make sure you don't blow your wad in just two pumps. The girls will want to see your cock go in me and we need to keep it up without you losing it. Do you think you can play for half an hour? How fast do you normally cum?"

"Uh... the first time?"

"Yeah, the first time. The second time will probably be Natalie. Stephanie is her maid of honor and is setting this all up, and said she would. But I haven't

actually

heard it from Natalie's mouth that she really wants one last fuck before she gets married on Saturday, so that could all fall apart. Reading between the lines, Stephanie is ready to have you take her to bed, too, or perhaps she wants to take

me

to bed, I don't think she's really decided that yet. So... how fast do you normally cum the first time?"

"I, uh, really don't know... how fast is fast? I guess if she's sucked me and I'm really turned on, pretty fast, but I can usually hold out until my client cums."

"But not always?" she asked, questioning my "usually" answer. I nodded in confirmation. "OK, good, so you have

some

self-control. Think about it, and decide whether you need to jack off and take the edge off before we get there. If we're there and you're too excited, we'll find a way to get you off before we perform. What about a second time? How long can you last then?"

"Almost indefinitely. After the first time, I can hold off and almost cum on command," I explained that I'd found that out almost from the start with Mary. After I'd come the first time I could get hard, and as long as I kept away from the

perfect

stimulation on my cock I could fuck her to multiple orgasms before I came a second time. But, if I shifted

just a little

, got the stimulation

just

right, I could come again almost on command.

"What about a third time? Can you get hard again after that second time?"

I scrinched my face a bit. "Not very rapidly. Sometimes takes a half hour or forty-five minutes. Even though I can eventually get hard a third time, it's hard for me to cum a third time, I'm just too numb. I can, but it takes a long time."

"Good, that's perfect, particularly if other girls want a fuck. If you can get them off without cumming yourself, then when multiple girls want one, you can do it."

"The way we are going to do this is to make sure when you're getting close, you quit the stimulation. If you're on top, you'll need to just stop and pull out, and you need to do it soon enough that you don't ejaculate at all. If you just stop, I'll know that's the case, and I'll take charge. Roll us over, a little fondling without jacking you off, letting you come back from the brink, and then I can climb on. I can rock back and forth with your cock in me, make it look like I'm doing more than I am, but let you continue to settle down a bit more. When you're more under control, then you can take over again. A good way to do that is to push me off and then I can get on my hands and knees and you can take me from behind, doggie style. That's a good one to really pull back and then push back in slowly. We'll position ourselves so that we're in profile so the girls can see your cock sliding in and out. We'll play that by ear, and see how much time we've taken. We may then need to do another position. If we go back to you on your back, I can climb on reverse cowgirl. They can see me finger myself while we're fucking so I can cum, and this time you can cum too. Whether they know it or not, invariably seeing that you came is important, confirming that it wasn't all just an act."