How I Became a Gigolo - Cover

How I Became a Gigolo

Copyright© 2013 by aubie56

Chapter 9

Erotica Sex Story: Chapter 9 - 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  

As the saying goes, "There was trouble in River City!" Though that was not the name of our city, that was certainly the situation that we were facing. Three older boys or young men were terrorizing the kids' make-out sites. The were beating the boy enough to send him to the hospital for an extended stay and were raping the girl sufficiently to force her to spend some time in the hospital. Needless to say, that was playing hell with my business!

The cops had started patrolling the various lovers' lanes, but that was obviously doing no good. The cops were using patrol cars, and all the bastards had to do was to duck out of sight until the car had passed. Therefore, I was going to have to find some way to defend myself and my date if I were going to stay in business. Carrying a gun was completely out of the question, and I knew nothing of knife fighting, so that was another option shot to hell.

About that time, I ran across an Internet story in which the hero made a big deal out of something called "stick fighting." The story made that sound like a promising option, so I searched the web for more information. Hell, learning stick fighting was going to take the same kind of commitment of time and effort as any other martial art, so I knew that was not going to do me much good.

However, I did get an idea from the stick fighting suggestion: I tried a piece of iron pipe about an inch in diameter and 18 inches long. I had both ends of the pipe threaded and put a cap on each end so that the pipe would not slip out of my hand. This provided me with enough mass in my weapon so that I figured that it would make up for my lack of skill and clumsy style. I knew that I would be at a big disadvantage in a fight with three men, but I hoped that an aggressive style and surprise would make up for a lot of that. I did take the time to work out every day with my new weapon, and that helped a lot. Now that I had a weapon, I was ready to return to business.

Jenny let it be known among her high school girl contacts that I was prepared to defend us if the situation came up. Apparently, my reputation as a stud quickly overcame the fears of my potential customers and business quickly returned to its previous level. All of this took about four weeks, and I was really pissed off at the loss of income, so that I was almost hoping that I could meet the Lover's Lane Gang. Ah, the foolishness of youth!

I took my pipe weapon with me on every one of my dates. Each time, the girl was surprised to see me carrying the section of pipe, but she relaxed when I told her it's purpose. Very quickly, the word got around that a date with me was a safe date, and the girls relaxed as soon as I got into the car. I don't know if the word got back to the Lover's Lane Gang or not, but I was never bothered by an attack from them, and, in my foolishness, I was kind of disappointed. Oh, well, I was able to live through that disappointment.

Meanwhile, my dates with the older women were totally unaffected by the existence of the Lover's Lane Gang since I always met the woman in her home. I picked up several more regular customers in the over-40 crowd to supplement my regular meetings with Ruth and Helen. That was strictly by word-of-mouth advertising, and I think the stories about me and my prowess improved with each retelling.

For example, a woman I had never met called Jenny at the beauty shop to arrange a date with me. She was a little reluctant when Jenny told her that she would have to come by the beauty shop to sign a paper. The woman finally showed up, signed up, and left a photo so that I would know who I was meeting. That's how I met Mrs. Janet Flowers, a woman who was only 32 years old. I was really startled when I found out her age and that she was married to a very successful businessman who rarely traveled.

It was only after I visited Janet for the first time that I found out the details of her unusual arrangement with her husband. It turned out that he was gay, and had only married Janet for windowdressing. On the other hand, Janet was about as hetero as it was possible for a woman to be, so she had to make some sort of arrangement to accommodate her needs. That arrangement had originally been a liaison with a young man who worked for an international corporation. She had her tubes tied to prevent pregnancy, so that was no problem. The liaison had worked for six years, but finally ended when her paramour was transferred to the UK. Janet had become desperate after about six weeks of doing without sex. That's when she heard of me and decided to try me out.

I met Janet at her home one Tuesday morning, and we had a long conversation while sitting in her living room before going any farther with our date. That was when I found out the background on Janet's sex life and why she had contacted Jenny to arrange for my services. Janet was a friend of Ruth Jackson, my first and probably most enthusiastic client in the older age group, and Ruth had recommended me. Uh-oh, I knew that I had better be at my best in order to live up to the level of recommendation that Ruth would have given.

That was also when I found that I had a time limit on this first visit. I had to be out of the house before 1:00 PM because Reginald Flowers was entertaining his boyfriend at home that afternoon. Janet wasn't concerned, but Reginald, her husband, was uncertain of my discretion. Later on, after he got to know me, that situation might change; however, I was emphatic in my statement to Janet that my services were not open to the gay community. I just didn't swing that way!

Once we had gotten reasonably comfortable with each other, Janet led me to her bedroom, which was separate from the one occupied by Reginald. Over the summer, I had had a growth spurt, which did nothing to mar my looks, but did add almost 2 inches to my height. The result was that even though I was still legally a child, I could easily pass for a young man in his early 20s. As soon as we reached her bedroom and Janet had closed the door, an option I left to her, I embraced her and opened with my standard deep French kiss.

I don't know what she was expecting from me, but I could not detect any hesitation on Janet's part as she returned the kiss. The day was quite warm and the air-conditioning was running, so Janet had been dressed comfortably in a very light wraparound dress which I likened to a sarong. The only fastening holding the dress closed was a large bow knot at her left side. I could not resist the temptation to untie the knot and allow her dress to fall open.

To my delight, Janet had been wearing nothing under the dress, and it kind of unwound as it fell open and dropped to the floor. This left her wearing only some sandals with a small heel and some hoop-hearings. I found the combination to be very enticing and made no move to have her remove any more of her accoutrements. The only blemish on Janet's body was that there was some slight sag in her D-cup tits, but, for me, that only added to her charm.

Once I had Janet's clothing removed, she started to work on me. She seemed delighted to find that I, also, had foregone any underwear, so that I was soon wearing nothing but a smile and a fierce erection. Janet exclaimed when she saw the size of my full erection, "My God, you are monster compared to Bob! I can hardly wait to feel that tool inside me!" As you can imagine, that gave quite a boost to my ego.

Janet embraced me while we were still standing beside her bed in such a way that my erect cock was pressing against her pussy. She had stood on her toes so that my cock slipped between her legs, and she was straddling it as if it were a pole. Janet squeezed hard with her thighs so that the length of my cock was pressed into her pussy slit, and the sensation was almost enough to make me come immediately. I managed to restrain myself, but it was "hard" work.

Somehow Janet managed to remove her sandals by only moving her feet, but the effect on my trapped cock was very nearly the equivalent of a jack-off session. Again, I managed to hang on to my dignity and kept from squirting, but it was even more of a struggle than the previous exercise.

Janet twisted her body and fell back onto the bed. She pulled me down with her with my cock still trapped against her pussy. I managed to break my fall with my hands, so that I did not land on her chest with my full weight. That probably would have been a disaster, but I got lucky. Fortunately, my cock did not get jammed into the mattress because of the thickness of Janet's buttocks and pelvic region, but I did feel just a bit of contact with the sheet.

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