Gigolo Ch. 1

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This is a true story and only the names have been changed. Let start by saying I am not a bad person. Some guys call me a loser, or a dick for having sex with older ladies, but I will explain my reasons for preferring older ladies. When I was high school and even college, I was fairly funny, and popular, but every time I went to make the move on girl you know the one, the one that’s either going to make it or break it, will the girl would always say the same fucked up thing.

‘You’re really nice, funny, and cute. And someday I love to meet someone like you, but you like a brother. You’re my friend.’

I hated that word ‘Friend’, it means you get all the fucked up jobs like listen to her problems about some prick she loves and hates at the same time. The having to try and comfort her and get a little feel at the same time. But she gets pissed when she finds out. Friends are fucked!

Well like I said this was the same all through High School, and then in my fourth year of Business at Berkeley I was getting tight on money and thought I was going to have and drop out. But then a bud of mine jokingly told me about this ‘Service’ that helped young guys make money. To him it was all a big joke, he was on the football team and tagged bitches left and right. But he must have known something about it because he always had good money, not rich, but always enough to go drinking, and still pay the bills.

One day after he had told me about this ‘Service’, I was helping him with some of his laundry mixed in with mine. I was running through his pocket, I had found some money, nude picture had taken of bitches, and panties of recent scores before so thought what the hell. He was often so drunk he didn’t remember anything so I’d keep what I wanted and throw the rest away. Well like I was saying I was running through his pocket when I found he had left his wallet in his jeans. I opened it, he had six twenties I pocketed. He hadn’t came in ’til about an hour before I was going to do the laundry, so I knew he wouldn’t remember what was in his wallet, and often girls picked his pockets before I could get to it.

I kept poking around and out fell a small piece of paper. It was folded quit tightly and tucked far back under his ID. I opened it and there was a single word ‘Service’ and it had an Oakland number. I wrote the number down on my hand and return the fold to the wallet. I sat the thinking about all Jay had said about going out with old ladies and making a quick fifty bucks. I thought he was just bull shitting, cause we were both pretty fucked up drunk. I finished the laundry and returned home.

Jay was still dead asleep, as I opened his room and dumped his clothes on the foot of his bed. I shut his door and went to my room. I shared my room with another guy, he was a dork I hoped every night I wasn’t as bad as him. But he and I did get along. We played D&D, Computer games, and watched Star Trek. James, my room mate was not home, he was at the Library, or at campus doing something as always. I looked at the number and didn’t want to think about it anymore. I picked on the phone and without thinking I dialed the number the phone rang, and I was about to hang up when I voice answered the other end.


I hesitated, but then spoke up.

“Uh, yes my name is Derrick. My buddy Jay gave me this number said I might could in for an interview. I’m looking for work and he said you might could help?”

The lady’s voice sound extremely calm, and as she cleared her throat she began in a commanding tone, like a teacher.

“Well Derrick, could you come in today?”

I looked at the time my classes were done but I had planned to go to the movies, but answered her anyway.

“Sure, where are you located?”

The lady gave me directions to an area pretty nice in down town Oakland. I knew the offices around there where almost all lawyers, and doctor at first I was a little nervous.

“Oh, yes one more thing Derrick. Do not say anything about this until we talk to you here, and please do not bring anyone with you.”

I told her okay and asked who I should ask for?

“Don’t worry, just come to the office and tell them your name.”

With that she hung up the phone. I changed my clothes, and dressed for a business interview in my best slakes, and shirt. I felt dumb, I didn’t really know what to wear if this was what I thought it would be. I got on BART and followed her directions, I walked into the office building and looked for the office.

Next to the office was blank. Just a number no office name. I got on the elevator and went to the floor. I walked to the office, and opened the door there was a desk, I nice looking older lady maybe 39 or 40 sat there working on a computer. I walked up to the desk and cleared my throat to get her attention.

“Yes? Can I help you?”

Her voice was velvety and soft. I nodded and answered with name and added.

“I called earlier, I am expected.”

She nodded her blonde head, and licked her thick red lips slightly, giving me a little surge through my cock. She turn and picked up a phone, illegal bahis I couldn’t hear what she told the other person one the other end of the line but, soon after she hung up the door leading to the back office opened.

There another older lady maybe 38, but I couldn’t be for sure. She smiled a full smile white teeth ringed by peach colored lipstick. I rose as the lady motioned for me to follow. I watched her ass switch from side to side, and her reddish brown hair wave at me. She lead me to a chair and moved around the desk to face me and she sat in a large dark red leather chair she introduced herself.

“My name Miss. Nina Harmon. You can call me Miss. Harmon or Nina.”

I smiled and reached out to take her hand, I thought quickly and lowered to gently kiss the back of her hand. And then waited like a gentleman for her to set. Nina smiled and nodded.

“Very good, you have manners. Something young men don’t always have that. Your friend Jay for example. He had to go through much training before he could be put on the list. You, I don’t think will need nearly as much training.”

I smiled and spoke up.

“So can you tell me this ‘Service’?”

Nina smiled and took a sip of water from a fine lead crystal glass.

“First tell me Derrick, what did Jay say about our little business?”

I felt a little nervous, Jay could have been fucking with me this might have been some kind of church. I spoke invasively.

“Well he said that he made money keep ladies entertained. He took them out sight seeing sometimes, and show them places nice to eat.”

Nina smiled and nodded.

“You are good Derrick. Now I hate to ask this but for my protection and my whole business’. Are you in any way involved with law enforce? Or any legal parties?”

I shook my head and understood what she was asking.

“No Miss. Harmon. I am in no way involved with law enforce, legal parties, or an other undercover sting on you or your business. I am just looking for some money and looking to have a good time.”

Nina then relaxed and began to explain things.

“Well then Derrick, first thing we are an escort service. We provide ladies with the company of both young males and female. Depending on the clients wants. It is not always sexual, often a lady might ‘date’ a young man a few times before anything sexual happens. We charge a fee, usually through cash or out of county accounts. I will not lie to you, not every call you get is going to be a lady you’d want to be with. That is where the training comes in. We teach the men and women how to, perform when needed.

So what do you think so far?”

I sat there happy to be told the truth of things.

“Well Miss. Harmon,”

“Please, Derrick. Nina. I only like Miss. Harmon when I get fools like Jay.”

I nodded and continued.

“Well, Nina. I am glad that you are honest with me. I feel honest is an important thing in a business like this, between employee and boss. How am I paid?

Nina giggled.

“A true professional. Tell me about yourself first, please? I think you be more then able to fill the bill for us.”

I relaxed a bit and told her about my dislike of young girls, of their stupid childish nature. And came clean in the end. I needed money, and was willing to work, if the price was right. I told her about my being in college studying Business Administration.

“Well Derrick, a lot of the pay depends on a few things. First you must show us a clean bill of health. No drugs, no STD’s! Second after your provide that paper work, we take you out for a test drive. Myself or one of my partners will take you out for dinner to see how you react to proper settings, then after dinner we go back to a hotel, and test you other skills. If everything is good at that point, a determination is made as to much and what kind of training is needed if any. I will tell you now though every person whose came through that door, has had to go to some kind of training. Jay took two full weeks.”

I nodded, and asked a few more questions.

“Well do I have to pay for the STD, and drug testing?”

Nina shook her head.

“No, we have an office we send you to. No out of pocket for you.”

I nodded and asked another question about the pay.

“Well let’s say I am at least as good as Jay on the pay department. How much would I make?”

Nina smiled.

“Again with the money you will be fine at this job. Okay saying you are at lest as good as Jay, which I think you will easily outdo. You would bring home a minimum of $100.00 a ‘date’. That is even if there is no sex. If there is sex, you’d about $250.00 a ‘date’. But with you skill and charm I’d say you’d start at $150.00 a ‘date’ and with sex at $300.00. And some depends on the ladies too, each lady is screen here first and we tell you before you head to a ‘date’ what to expect on looks. If the lady were, let’s say really old, and you were will, you could, no sex at $250.00, sex maybe as much as $350.00 or $400.00. Big ladies, old ladies, ladies with unusual physical defect all get you the high end, because it is hard illegal bahis siteleri to keep guys for them.”

I nodded.

“What is sex in your definition?”

Nina cleared her throat.

“Any sexual encounter. Including her giving you a blow, you finger her, her masturbating you, or you masturbating for her to reach climax. It is a little hard for male escorts, because if a guy went to girl it would over when he came, but since you are there to please the lady, it is harder. But we will teach you how to tell the lady, “look you’ve got off, anything more will cost extra.” So don’t worry about that.”

I nodded and asked just one more thing. I was sure now this was what I was looking for in a job. Now I could quit that fucked up job at the video store, if things went well.

“Where do I have to go for the tests?”

Nina nodded and pulled out some papers, and started writing a few things. As she wrote she said one more thing that kinda blew me away, but I guess it was a normal thing.

“Okay before I send you over there I need one more thing. Could you lower your pants and show me your cock?”

I stood a little nervous, what if I wasn’t big enough? What if I couldn’t get hard?

“Nina, I might not be hard, this is a little nerve wracking. You know?”

Nina smile and stood walking around the desk.

“Of course I understand. It’s okay I need to see it limp, first. And don’t worry I can make it hard.”

I lowered my slack. And then the boxer brief fell o the floor. I was limp as I had feared.

“Nice pants Derrick. I was going to comment on them when you came in.”

Nina took my limp cock in her hand and held it there looking at it taking mental measurement I guessed. She then lead closer and gently blew on the head, her breath was warm and soon I felt a stirring. Soon my cock rose be itself outta Nina’s hand and slammed against my belly. Nina looked pleased and smiled. She then stood and walked over to a small bar sink and washed her hands.

“It looks every nice. Every nice indeed. Most guys it takes a little while to get hard. I see you trim it nicely. My advise if you start working for us, it good measure to simply shave it all, we can show you how as not to hurt yourself. Body lice is not common but better safe then sorry.”

She then turned and handed me the paper telling me how to get to the office for the testing and that the office would call her with the results. It would take about two weeks and then she would one way or the other, if I passed or not.

Nina showed me out and gave me a little pat on the ass, telling me.

“Now make sure and head over to get the test.”

I smiled to the ladies and left. I hated needle and knew there was no other way, but it wasn’t too bad. I peed in a cup and had to give a hair sample for the drug test, but only one good sized vial of blood. I went home and waited.

The two weeks dragged by, but I didn’t call Nina and I heard nothing from her. Jay seemed to know nothing either. Nina probably kept employees from knowing each other. Or at lest the ones she respected. I was lying in the bath tub, dreaming of this girl I had seen on the internet, a basic porn girl but she had a great body and what she was doing with it was more then I needed to fantasize about. As I lay there I heard the phone ring, luckily James was home and was great about writing very clear notes.

Soon I heard a voice clearing his throat as James came to the locked bathroom door. He always clear his throat as a kinda of unspoken sign that someone was coming toward the door just encase a guy was busy you understand.

“Derrick, a lady was on the phone for you. I wrote down her name and the number. She said it was about a job?”

I called back to James and began to get off of the tub. I dried off and slipped on some underwear, and a robe. Exiting the bathroom, I went to our room, James was there on the computer download some porn pictures, e-mailing a D&D buddy, and doing some homework. I slipped into some jeans and removed the robe. I walked over behind James who handed me the phone message. It read simply,

Miss. Harmon


Called asked to please return call ASAP.


James was not one to make detailed or long messages but always took the important information. I pick up the phone, James was often to wrapped up in his computer to listen to something as unimportant as a job phone call. Plus he wore headphones, and listen to music all the time. In front of him on the wall was a mirror so he could always see anyone coming in or standing behind him.

I sat on my bed and dialed the number. A voice answered it was the secretary.


I answered in a claimer voice then before when I called.

“Hello, this is Derrick. I got a message that Miss. Harmon had called?”

The lady’s voice went cheerful and happy.

“Oh, yes Derrick. Let me transfer you to Nina.”

I waited as the line connected and I heard Nina’s voice.

“Hi, Derrick. How are you?”

I read in voice that things must have went will.

“Fine canlı bahis siteleri and yourself?”

Nina explained that she had had a back ache all day.

“Well, anyways Derrick. I just waited to tell you phase one is fine. Your tests came back completely clean. I would like to set up the second part, by having you meet someone for dinner. If that is okay?”

I laughed.

“No problem at all. I’m very happy things came out fine, I’ve been very excited the last two weeks.”

Nina too laughed and continued.

“Well would tonight be alright. I know it’s kinda short term, but I was hoping we could get you through the test and get you out working.”

I thought about the time it was only 4:00pm, and I hadn’t ate yet. But I had planned on studying some with a classmate. I guess I could always call him and tell him I had to change plans.


Nina paused a moment.

“Are you sure, I mean if you have other plans. I don’t want to come between you and school.”

I spoke more firmly and confident.

“No, no. Tonight is fine. Should I meet this person somewhere or should I come to the office.?”

Nina spoke up quickly.

“No not here. One thing Derrick you will almost never ever come here to get a ‘date’. Ever. I will give you the lady’s address, and directions if you need.”

I apologized for have said anything about picking up someone at the office it was dumb of me to think I would go to the office and walk out with a lady.

“Okay I know area pretty good. Does she know I coming?”

I asked Nina. Nina told me everything will be ready and if anything went wrong she would call in plenty of time to change plans. I had three hours before I had to pick up Miss. Lee. She was single so I didn’t have anything to worry about and she would the one to test my manners and skills. Nina told me not to worry about money, and dress nice, kinda like I had dressed for the interview. Nina said that tomorrow Miss. Lee would report her finding and Nina said she would be in touch tomorrow, but if I had any question, I was free to ask Miss. Lee and soon as Miss. Lee told me ‘Good Night’.

I hung up the phone and began to think about things. What clothes I needed and I would need to get on my computer, a heavily custom built thing, that James had made for me, a hobby of his building computers for people. His was a monster able to do things I think were illegal in most states. Mine was not nearly the big. I sat and got exact directions to Miss. Lee’s place. I then dressed in a nice pair of Dockers’ and a nice shirt, I wore leather shoes, and grad some condoms, a thing I hadn’t used in a while.

I walked across the streets and down to the next block to the parking garage. I had a nice little ’73 Firebird. Jay’s one quality, he loved cars. He had a Classic ’64 Mustang, that had been his Dad’s but had brought it to college. He work on mine anytime I needed and took as much care with mine as his own. I was surprised.

I didn’t drive the Firebird too much, but Jay kept it running in top running order. I started it, it purred like a kitten, and shifted into first. I pulled out giving a little wave to guard and pulled out heading for the local Mobil. The only two credit cards I had a Mobile card, a Visa with little $500.00 limit, I needed to make a payment on bad! I drove to the Mobile and filled up, I had a good 45 minutes, but knew it would take a little bit to get to Miss. Lee’s.

As I drove to her house I wondered what she looked like. I had been so excited about everything I hadn’t even thought to ask Nina. But she could be too bad she was a partner of Nina’s. But then again made she was the first test, Fuck an ugly girl and make her like? I got a little nervous and grabbed a piece of gum. As I chewed and drove I began to think maybe this was the wrong thing to do. But before I knew it I was parked across the streets from some very nice apartments.

I spat out my gum, and gave myself one last quick look over and a little squirt of Hilfiger. I got out the sun was going down, but I kept my Oakleys on as I walked up to the intercom and pressed Miss. Lee’s number. I had gotten a small thing of flower nothing to big, but a nice touch I thought.

A voice answered the intercom.


I stepped a little close and spoke clearly.

“I’m Derrick.”

The sound of someone exhaling, as if they were smoking came back.

“Okay third floor, come on up.”

The door buzzed, and I pulled it open. I crossed the lobby, a richly designed room, with small sofas, of deep burgundy colors, and lush green fern grew in huge pots. The wall were a lovely dark green and paintings hung here and there. Over all it was an impressive room. I entered the elevator and went up.

I open the door to small hallway, and found Miss. Lee’s door. I knocked sharply and waited. The door slowly opened and there stood an Asian women. She was about 5’3″ and wore a tight black dress which revealed some of her cleavage. She had nice tits, but I guessed they in a push up bra. Overall she was not too bad, but she had a face I would not want to wake up to every morning. Miss. Lee had high cheek bones, and she wore a little bit too much make I thought. Her lips were painted red, and she had her black hair in a bun, but I could see brown high lights.

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