How I Became a Gigolo
Chapter 5

Copyright© 2013 by aubie56

Erotica Sex Story: Chapter 5 - This is the story of Billy Weston and how he became a professional gigolo at age 14. His sister Jenny appointed herself as his pimp. At first, his parents thought that he was still doing lawn care until his mother found over $8,000 stashed in his room. That's when things got a little complicated.

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   mt/Fa   Consensual   Heterosexual   Humor   Incest   Brother   Sister   First   Oral Sex   Prostitution  

Janice was a bit tentative at first, but I let her set the pace since she was paying for it. I wish I could say that it was my great technique that moved us along fairly rapidly, but, in all honesty, I must admit that Janice proved to be very horny when she warmed up a bit.

Janice took her own blouse off simply because I was trying not to push her too hard, but it took less than 10 minutes for us both to be naked from the waist up and locked in a lovers' embrace. Neither one of us needed instruction in French kissing, so we took that route very early on in the date. We kissed for a few minutes, and then I slid my hand up to grasp her right breast. It was as if a starter's gun had been fired and we were off to the races. Jenny had helped me to learn how to remove my date's panties while still sucking on her nipple. Thus, a few minutes were saved, and Janice was already dripping lubricant from her pussy.

Janice was wearing stockings with a garter belt instead of the usual pantyhose. I presumed that she was doing this because she felt sexier dressed that way. I can go along with pantyhose in a working environment, but I much prefer the separate stockings and panties for a heavy date. Again, it was Jenny who clued me in on the relative advantages of the different kinds of female attire.

I pulled her panties down to her knees and paused long enough to remove her shoes. Jenny had shown me what an aggravating nuisance high heels could be when I was trying to remove my date's panties. I got past this little roadblock very easily and was ready to progress to removing her skirt. I had no intention of removing her stockings or garter belt unless Janice specifically requested it. It had never happened to me before in real life, but those porn movies that I had seen on the web sure were sexier when the woman was wearing stockings and the garter belt. I wanted to go whole hog on my own enjoyment if I could get away with it, so I waited for Janice to tell me her preference.

Her pussy was as clean as a whistle (I saw that phrase in a book once), and it certainly looked perfect to me. She had the classic Camel toe with no sign of her inner lips or her clit. All I could see was her two very puffy outer lips with a pristine slit separating them. I had heard from some of my friends who considered themselves to be very sophisticated on the subject of pussies that a woman who did not have her inner lips at least showing a tiny bit just had to be too young to appreciate sex. Well, I had always thought that those guys were full of shit, and now was my chance to verify my assessment of their sophistication. Anyway, I was a fan of the classic Camel toe, and I was delighted to see it attached to Janice.

Janice was wearing a kind of wraparound skirt that was very easy to remove. I had that off her in only moments after removing her panties. You may note my careful consideration of my client because I dropped all of the clothes removed from Janice onto the front seat where they would not be soiled by whatever might be on the floor. I doubt that Janice made any note of what I had done with her clothes, but I was sure that she would appreciate my consideration later on when she got dressed to return home.

Janice wanted to remove my trousers, but she could not conveniently reach my shoes. I had planned ahead on that and was wearing some black loafers that simply slipped off my feet. I was not wearing socks, and I was not wearing underpants, so all I had left to remove was my trousers. Janice took delight in unfastening my belt and opening my fly. She squealed when my already stiffening cock jumped through the open fly and pointed at her face. Undoubtedly, she had been expecting some sort of underwear, so she was caught by surprise when the Jack-in-the-Box jumped out at her. We both laughed at her reaction, but quickly returned to our main reason for being parked where we were.

She caught me by surprise by grabbing my cock with her hand and pulling me to her mouth. I must say that I was truly impressed by the quality of the blow job that she gave me. I called for her to stop before I came in her mouth, but she pointedly ignored me and continued with the blow job. I don't know who or how many guys she had blown, but she did seem surprised at the quantity of jizz that I deposited in her mouth. Just as any hooker would have been expected to do, Janice opened her mouth and showed me the jizz collected on her tongue just before she swallowed it. This convinced me that my client was a woman of experience, and I was anxious to see what else she had to show me.

She wiped my cock with one of the towels so that I would not drip on the upholstery, and I slid another towel under her ass to collect the drainage during and after our fuck. At this stage in my life, it took me about 15 minutes to recharge my jizz supply, so this was the perfect opportunity for me to eat her pussy. It was a thing of such beauty that I was determined to put my mouth on her pussy unless she flatly objected, and I did not expect that to happen.

In an effort to return to our previous activities, I slid down onto the floor to kneel there and put her ankles across the top of the back of the front seats. That boosted her pussy plenty high enough for me to reach the whole thing so it only took a few moments for us to achieve the proper positions. Janice was not surprised because I had told her what I intended to do, and she seemed thrilled by the prospect. She claimed that her pussy had been eaten several times, but by boys who really did not know what they were doing. I assured her that I intended to make this a special occasion for her enjoyment.

I started out by licking her outer pussy lips, going from the right lip to the left lip and back all the way from the bottom of her slit to above her clit. I made about 10 passes on each outer lip before I tried anything else. By the time I was only halfway done, Janice was drowning in the spirit of the thing. She was panting so hard that I half expected her to hyperventilate, but that didn't happen. She was moaning in sync with my licking by the time I finished my total of 20 strokes and switched my target.

This time, I traveled up her pussy slit putting gentle pressure on it with my tongue. The second pass was enough to force it open so that I could reach her inner pussy lips. When I make contact with them, I thought she was going to explode! She had a major orgasm right then and never seem to come down completely from it the whole time that I licked her. She was gushing liquid from her vagina and bouncing around so much that I could hardly maintain contact with her.

When she did come down enough so that I knew I would not injure her, I grasped her clit with my lips and sucked as hard as I could. This pulled her clit from the sheath far enough for me to nip it with my teeth. Yes, I have practiced this with Jenny and knew that I was not going to hurt my client. That nip was enough to make Janice scream loud enough seemingly to be heard for miles. Several other cars were parked in the general vicinity, and Janice's scream was loud enough to cause some horn honking in response. I couldn't help laughing, but Janice never noticed.

I sucked on Janice's clit for a little longer and did gently bite it a couple of more times, but I started backing down my stimulation of her pussy, so that she would have something left for the fucking that was coming up. I definitely did not want to burn her out too soon. I fully intended to give Janice her money's worth!

It was not an easy thing to do, but I did manage to squeeze in beside her to cuddle with her while she came down from her series of orgasms. That woman held onto me as if she feared that one or both of us was going to float away. There was no doubt that I had gotten her full attention.

I didn't want this date to run too long and chance making trouble for Janice when she got home. Therefore, as soon as I thought she was ready, I suggested that we proceed with the climax of the evening. Supposedly, Jenny had already made sure that Janice was fully protected from pregnancy and had no STDs (Sexually Transmitted Diseases). Nevertheless, I did ask her the necessary questions because I wanted her to realize that I was concerned about potential consequences. She assured me that she was taking the Pill, and that she had recently been tested and cleared of STDs.

 
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