Why I Became an Escort

We left my house and my old friend and I roamed through the higher end stores in our town. Boutiques, lingerie shops, jewelry stores. We stopped for lunch at a new, and very expensive restaurant for lunch and cocktails. Several times, when we were alone, she would give me advice on how to flirt, entice, seduce and generally make my client want me for the night and for repeat business.

"Remember Gidgit, you usually only get one night to make them want to be a repeat client so make that night something for them to remember. If you leave them wanting more of you it's like reeling in a really big fish that you catch over and over."

We ended our shopping day by getting our hair, nails and bikini wax done at a mini spa. I had not had my hair done by a professional in years because of the cost of a hairdresser but, because of my new occupation, Deb said that it was essential to look good.

"Your skin looks blemish free so a facial can wait but in the future we will be doing the full spa treatment, a lot", Deb said as we left the hairdresser and headed to my home to unload several thousand dollars in clothing, lingerie, shoes and jewelry. I was a bit overwhelmed by the scope of her knowledge of the trade. I was even more overwhelmed at how much my best friend had spent on me today.

Nearing my home I asked, "Deb, are you sure that I will need all these new clothes, shoes and jewelry?"

"Honey this is just to get you started. By the time you get comfortable in the business you will have to turn one of your guest rooms into a walk in closet. Now there is one more thing that I want you to be comfortable with. There are a lot of gay and bisexual women out there that will be paying for your services. Are you comfortable with having sex with another woman?"

"No I'm not. That's something I wanted to discuss with you. The Debra I knew from high school was just into men. When did you start going both ways if I may ask?"

" Actually it was several months after high school. I was just a freshman in college and had a date with a married couple. I had never had a threesum with another woman but I had been with multiple men. I had been with only men at that point but the money they were offering was too good to pass up. They were an older couple and he was much older than she was and he couldn't satisfy her because he had trouble staying hard. When we went into their bedroom it was just normal vanilla sex until he finished. After he was done the wife wanted me to service her as well. I had already been paid so I thought that I couldn't back out then so I just closed my mind and did the things to her that I enjoyed. I guess that I was good enough because they were repeat clients for several years. Gidgit, you will have to get used to being bisexual. Is that going to be a problem for you?"

We were almost at my home and I needed to get this one issue behind me. "Of course it's a problem. I have never been with a woman and I don't know how to seduce one. If I'm going to be successful I need to get over this hurdle. The how is the problem."

Deb smiled as she said, "Just leave that to me."

We pulled into my garage and with Debs' help we emptied her car of all my new purchases. I was like a child on Christmas morning as I went over what my friend had spent on me. Mentally I added up the cost to my friend's credit card as I tried on some of my new clothes. I was naked while trying on some sexy bras when I asked, "Deb, are you sure that I will be able to pay you back? All of this must have cost you thousands."

"Don't worry about it Gidgit. Your money worries are almost over. Once you get a few clients of your own the money won't matter any more. Now, we have been working hard all day shopping so let's take a shower, together, until we are squeaky clean."

"Together?" I said as my best friend pulled her electric blue dress over her head. She bent over at the waist and unstrapped her shoes from her ankles. I, of course, had seen her naked before while we showered after gym class in high school but she looked different now. Then I noticed it. She had no pubic hair on her pussy. I could see everything from her ass crack to her clit as she bent over and she was bald down there. Then she stood up and looked at me with that smokin hot look that she had perfected. She closed the distance between us and unexpectedly pinched both of my nipples. I flinched as the shock to my groin was almost electric. Then she giggled as she slid her arms around me and kissed me softly. Her lips were pressing slowly as her breasts moved against mine and her hands moved to my ass and squeezed my butt while she ground her pubic mound against mine. The quickness of her seduction had paralyzed me briefly. I was also shocked to discover that I was turned on. Frankly the entire day had been a slow seductive turn on. The shopping. The cozy lunch and cocktails. The spa. She had been complimenting my body at every opportunity for the entire day. She had even touched me several times during the fittings. I thought it was just casual touching but it wasn't. My friend had spent the whole day gently seducing me. Now she was moving onto a more serious seduction. We were going to fuck after our shower I was sure.

I could feel the wetness in my pussy when we broke our embrace. Deb gave me that sultry look again as she said, "Now, about that shower?"

We spent time in my shower cleaning the already clean parts of our bodies. I mean clean is clean right? We spent a lot of time rubbing my shower gel into each other's breasts. Her nipples were like little gumdrops on her areola when aroused. Mine were more rounded, like the shape of cherries or grapes. Her areola and nipples are very light colored, only a few shades darker than her breasts. Mine were very dark, the color of dark chocolate. Both pairs of our breasts stood very proud with no sagging.

Probably because I had been celibate for so long it didn't take much for my first orgasm to roar through me. My legs were quivering as Deb expertly brought me to a finish with her fingers on my clit. I was totally in heat then as I turned the water off and we dried each other off before getting into my bed. When we laid down she pulled my face against her pubic mound. Although her pussy and ass crack were bald, her pubes above her clit were trimmed short and in the shape of an arrow pointing down.

"Just do to me whatever feels good to you. Just a few pointers though. I love having my ass hole rimmed and when you get me really revved up my clit loves to be spanked or bitten. Now go to it Gidgit!"

I did. I found out that this woman was very susceptible to oral orgasms. She loved my fingers and tongue to continuously move across her pussy and ass. While I was working her up for her fourth, (or was it her sixth?) orgasm I recalled something that I had read in a womans magazine about butt play during sex. I smiled as I stuck my totally wet finger into her asshole and she exploded in orgasm.

"AHHHHH!" she screamed. "All the way! Stick your finger all the way in my ass!" I did and she came even harder. "That's it. Now put your thumb in my pussy while you lick my clit. Finger fuck both of my holes. AHHHHH!! Yesssss!!" Deb shook like she was having a seizure then simply collapsed, her legs splayed apart as I watched her sexy body quiver and shake in post orgasm aftershocks.

I couldn't believe how vocal Deb was when she was cumming. My ex had never made me feel like that. It was like her sense of reality had left and she entered another realm. I smiled as the thought entered my mind that I had also very much enjoyed giving my friend this pleasure. Deb started to move. She was still on her back and her arm's moved above her head. She looked like a human X on my bed. She blew some air up to clear some of the hair that had covered her face. Then she looked down at me.

"I thought that you had never had oral sex with another woman."

"I, I, I hav..., You are the first one. Was I ok?" I stuttered.

"Gidgit, honey, that was the best I've had in a long time. Almost a perfect fuck."

"Almost? I did everything to you that I like. I did add the butt play. I've never had anyone play with my butt but I read about... What could I have done that would have made it better?"

"I bet that no one has ever found your G-spot, have they?"

"G-spot? I thought that was only in fiction. Something that guys put into their erotic porn stories to make the sex seem hotter.

"Let me get this straight. No man has ever massaged your G-spot?"

"Ummm, no. Where is it?"

Deb laughed. "Oh my god! You are such a virgin! Ok since I'm in the right position, slide your middle finger into my pussy, palm facing up. That's it, now curl your finger slowly until you are massaging the upper wall of my vaginal canal. That's good. Now feel around until you find a slightly raised patch of wrinkled skin. Right there. That's my G-spot. Every woman has one and most men couldn't find it with a detailed map. If you ever do find a man with a respectable cock that knows how to give you a G-spot orgasm, hold onto him. He is more rare than a unicorn."

"Considering my new occupation, I don't think that I will be looking for a man very soon." I said softly as I massaged Debs G-spot.

"Oh Gidgit, I wasn't ready for this but since you are already down there. Ummm, you...can...rub it...or tap...on it...or...or...or, dam girl are you positive that... that... you. OH FUCK! CUMMING!!!" Deb started shaking like she was having another seizure only this time she simply tilted her head up and opened her mouth in a silent scream as her body shook. Within seconds she expelled a large quantity of fluid from her pussy. I thought it was pee but it didn't smell like urine. Was this a squirting orgasm? I wondered if I could induce the same type of orgasm to myself. Deb was so right. Sexually, considering what I had learned tonight, I was nearly a virgin.

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I had my first date that same week. He was an older business man that had been a client of Debs for over a year. She was booked solid when he called her for a date so she put the hard sell on him, telling him that I was her partner now and that I was new in the business. She guaranteed that he would be happy with me so he reluctantly went along with her recommendation. His name was Angus and he was some type of high powered executive in pharmaceuticals. Deb filled me in on him, his likes, his dislikes. What they usually did on a date. What they usually talked about while dining. What kind of sex that was expected from him. What kind of pillow talk they usually had and so forth.

Deb kept a detailed log of all of her repeat clients and she recommended that I do the same. We could cross reference both logs if we both had the same guy at different times she suggested.

The date with Angus was actually quite nice. He would only be in town for a short while so he would only need a companion for one night. He was the perfect gentleman as he escorted me to a fine dining restaurant. We chatted about several subjects, politics, local sports teams, his business outlook. He carried most of the conversations but I had a basic knowledge of all of it but his occupation. I let him lead the conversation when I had no clue what he was saying and just looked into his eyes, giving him the impression that I was fascinated by what he was saying.

Finally the night wound down and we retired to his suite. One thing I was quick to learn was that these high powered executives lived in luxury. Only the finest food, wine and accommodations would suffice. He had a top floor suite with an amazing view of the city lights. We relaxed with drinks out on his private patio with some more chat. He found out some of my story and I, his. He was forty eight and a lifelong bachelor and preferred to stay that way. He told me that he was married to his job so he would have been a terrible husband so an escort was a practical solution to fulfilling any sexual needs. He could afford me so to him I was simply another tool for him to use to relax after a long day.

He was a pretty good kisser and he took his time seducing me. Although he didn't have to seduce me. I was a sure thing but he still went through the motions. Our sex was nothing too athletic. His cock was normal sized but thicker than my ex and he lasted a long time. As he fucked me I mentally measured Angus to my ex and Angus came out on top across the board as a lover. A big plus was that Angus loved to eat pussy and my ex would never do that.

Take that dirtbag!

I was supposed to stay with him over night so we showered together to clean ourselves up and I wanted to give him an incentive for future business so, without him asking, I got on my knees and gave him a long sensual blowjob with the water raining down on us. I wanted my first client to be totally drained before sleeping with him. We fucked once again before breakfast, showered together again and I gave him another blowjob for making my first date so enjoyable. When I was getting ready to leave the room he tipped me fifteen hundred dollars and told me to tell Deb that one of us would see him the next time he was in town.

Fifteen hundred!!

I was on my way home when Deb called to check up on me. I was stuck in the city traffic when she called so I was able to talk. She asked me how my first date went and I gave her a glowing critique. She told me to keep the tip and use it to start a new account in a different bank than the one I normally used. As I was driving to deposit my first payment, minus Debs cut to pay her back and for the clothes and reference it hit me.

I was a high priced call girl/escort. A hooker. A whore.

And I was okay with that.

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After my first time with Angus it got easier. There were a lot of business executives that wanted company while traveling. There was even some local businessmen but I stayed away from anyone local. I wanted to stay anonymous to anyone that I happened to know because of my ex so I usually let Deb handle the locals. I was in the business for six months before I had my first woman client.

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She was around fifty five and an attractive lipstick lesbian. We met for dinner and drinks and she totally wanted to carry the conversation so I let her. Finally she asked me if I was okay with us making love in her suite and I assured her that I was more than okay with it. We went to her suite and she wanted to be the aggressor in bed. We rolled around in the sheets as I gave her at least ten orgasms. Then we had shower sex and she ate me as she plunged two fingers into my ass. Deb was the only other person that had dug the dirty out of my poop chute so it was somewhat of a surprise but in the end I actually enjoyed it. When we finished our shower sex she suggested that I should stay the night and she doubled my normal rate for my tip. I had no clean clothes to change into in the morning but what the hell. She was a hell of a fun date and the sex was outstanding so I did.

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My first couple was my first client that wasn't referred to me by Deb as her overflow. I actually met them while shopping for some new lingerie. She started a conversation about how hard it is to find comfortable bras in her size, (she had huge tits!), then the uselessness of some men. We had lunch and cocktails. We we're sending each other signals and before I knew it I told them what I did for a living and she propositioned me. I was very surprised initially, and very skeptical of someone that I had just met so I got her name and address and promised to meet her later in the day. When I got home I called Deb and she did a quick computer background check on the couple. They checked out as a local run of the mill married couple and not the cops so since I happened to be free that night I met up with them for drinks and dinner at a local club. He was a local dentist and she was his hygienist. We exchanged stories and I found out that their marriage was open but the only ones that were allowed to play with them were women, and she picked out which woman was allowed. It was a fun night as they both attacked me with fingers, tongues, several different dildoes and, I couldn't believe this, he even had a huge buttplug in his ass when we undressed. He was very well endowed and I was worried that his cock would be too big for me but he was gentle and used plenty of lube as he filled me up. His wife pegged him with a strapon dildo as he fucked me. After he came she immediately ate me out while I was still excited. It was a wild time for the four hours that I was with them. They took my name and number for further dates and we parted late that night. They were happy to pay my fee and even gave me five hundred for a tip so I was singing as I navigated the streets carefully to my home twenty five hundred bucks richer.

My first really big cock was a surprise. It was attached to a short, I'm not going to say fat but definitely overweight, CEO of a fortune five hundred corporation. He was one of Debs regulars and she was away with a client for a week in Denmark. She filled me in on his info and when she was finished she mentioned that this guy was huge.

"He has a really big horse cock Gidgit. You will need extra lube and make sure that he goes slow until you are comfortable. He loves to pound your pussy and, to make matters worse, he lasts a long time. I don't know how he does it but by the time he fills his condom you will probably be sore. Very sore."

She was right. I always figured that a big one would be eight or nine inches. He had to be at least eleven or twelve inches and as thick as a beer can. I used a whole bottle of anal-eze for my date with him. I must admit though that once I stretched to accommodate him the sex was incredible.

Deb was right. I was sore after Mr. Horsecock. For a week, but he tipped me a huge diamond bracelet worth several thousand so I went home and soaked my bits in my new hot tub.

My first black guy was another CEO. He was another of Debs regulars that I was fortunate enough to meet. He was handsome, wasn't that well hung but that man sure could fuck. He ate my pussy like a lesbian and could fuck for hours without cumming it seemed. He was patient and treated me like I was this porcelain doll. So tender. Oh yeah, he definitely knew how to massage my G-spot. Had I been in the market for a husband, he would have been at the head of the line.

I don't mean to make my life sound like everything was perfect. I am a woman so there were several days out of the month that I was out of service, so to speak. I had always been moody during my periods so I usually spent those days relaxing at the spa or updating my wardrobe. When I had been in the business for a year I took a short break with Deb. We spent a week in the Caribbean on one of those Disney cruise ships. It felt nice to be able to relax with my best friend. We caught up on how and why we had lost touch after high school along with how our lives had changed since those days. I told Deb during one of our heart to hearts while tanning topside that I was planning on quitting the business when I reached a certain monetary goal.

"What will you do with yourself when or if you retire Gidgit?"

"At this point I don't know for sure. What I don't want to happen is for this lifestyle to become all encompassing and something that I need to do in order to stay sane. I'm not really a slut at heart, although I feel like it sometimes. I was kicking around some ideas in my head one day and I have put a few feelers out there to invest in some real estate, specifically I'm thinking of investing in a high end resort somewhere tropical. Possibly a Greek island resort or maybe the South Pacific. Right now it's just an idea. With the right investor to partner with it would be a lot of fun I think. Maybe if I owned my own resort, if I felt the need, I could supplement my income occasionally by servicing a well chosen customer with some play for pay. Like I said, it's just an idea so far.