How I Became a Gigolo
Chapter 2

Copyright© 2013 by aubie56

Erotica Sex Story: Chapter 2 - 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  

Jenny flopped back into the position she had been in for our previous fuck, and I moved between her legs. She raised her knees and spread them as far as she could. That gave me a direct shot at her cunt, and I had no trouble finding the right place to put my cock this time.

Ever mindful of the hints that I had received from the previous time, I rubbed my cock head up and down in her pussy slit to make sure that it was wet with her lubricating oil. Jenny was dripping liquid from her cunt hole, so there was no question about having enough lube for me to penetrate her.

She must have really been in a hurry because she raised her hips and forced my cock head past her pussy lips. I guess that she had already started to adapt to my size because I slid right in with no problem. It felt good slipping past that ring of muscle just behind her pussy lips. Ah, that must be one of the greatest feelings in the world short of actually fucking.

It only took a couple of strokes for me to get all the way into Jenny's cunt. She must already be stretched a little bit, and when that was added to the mixture of her lube and my jizz, I had a very nice slippery track for my cock. Jenny was still tight enough that there was no problem about me pressing on her G-spot. I began to stroke slowly at first, but I sped up after a few strokes. Jenny expressed her appreciation for my technique by beginning to pant in time with my strokes.

I was in no great hurry to come, so I settled into a steady pattern of moderately rapid strokes. I don't know how long I stroked, but it felt like both only a few seconds and hours of stroking, when Jenny started to show signs of coming again. This time, she rose to the peak of her orgasm without me jetting into her.

Jenny panted faster and faster until she was out running my stroke rate. She began to twist up her face into a grimace, and she suddenly exploded with a loud moan that was obviously not a sign of pain. This had no direct affect on me, except that I felt her pussy muscles tighten up while she was in the throes of her orgasm. She drifted back to Earth and presented me with a smile that expressed total pleasure.

I had not come yet, so I just kept stroking at my same rate. Jenny got a pleased expression on her face and returned to her panting in time with my stroking. Jenny seem to have loosened up a bit with her grip on my cock, and I commented on that. She seemed to think for a moment and then smiled. The tight feeling around my cock returned as she consciously tightened her pussy muscles.

I can't express how much difference that made in the feelings I was getting, but it seemed to help a lot. I continued to stroke, and Jenny continued to grip and pant for a few more minutes. Then I felt her start to react to my strokes as if she were approaching another orgasm. That somehow affected me, and I felt myself getting ready to shoot. I managed to warn Jenny what was about to happen, and she said, "Come on, Lover. Give me your best shot!"

I took a couple of more strokes and let go with a major jet of jizz. That was all it took to put in Jenny over the top, and she began to come along with me. Her grip on my cock got so tight that I could hardly move, but it still felt like heaven! Both of us came at the same time, and I pumped so hard that I may have been in danger of pushing Jenny through the mattress.

When it was over, Jenny pulled me down for another one of her soul searing kisses. That did it! I fainted and rolled off of Jenny. I was not unconscious very long, but I was totally exhausted. Jenny and I slept for a few minutes, but hunger woke us up.

It was a long time since breakfast, so we were both ready for some lunch. We did take the time to shower together, and that was an experience I will never forget! We each thoroughly washed the other's naughty parts and dried each other off when we left the shower. Just in case that our parents might show up earlier than scheduled, we dressed enough to be decent and went to the kitchen to fix some lunch.

After lunch, we sat in the family room with the TV turned on. The latter was for camouflage against the appearance of our parents. We talked about ourselves and our possibilities for continued fucking. The prospects look good because Dad and Mom worked regular jobs during the week. Thus, we had time after school that we could be together with both of them out of the house. That was perfect from our point of view! We could fuck every afternoon after school if we wanted to. A reasonable amount of discretion should keep us safe from discovery.

Sunday was an off day for fucking because our parents wanted to make that a family day. That was actually a good thing for us because it gave Jenny's sore pussy a chance to recover: six days of fucking in a row was beginning to show on her as wear and tear. I probably needed the rest, too, but I never got sore. The one change I noticed was that my abdominal muscles seemed to get tougher. That must have been from all of the exercise during fucking.

Now that I think about it, I wonder why we were not caught. Mom looked kind of strange at Jenny on several occasions, but she never said anything. Nevertheless, she did make a point of being sure that Jenny took her birth control pills and visited her gynecologist on a regular schedule. I am pretty sure that Mom did suspect some hanky-panky from Jenny, but I assume she never suspected that I was involved with her. Anyway, we got away with it! Enough said on that subject.

By the time school was out for the summer vacation, Jenny and I had fucked so many times that I knew as much about it as she did. Jenny had spent a lot of time educating me on the fine points of foreplay and making out. We had spent a lot of time when we were not fucking with me learning the fine points of cunnilingus. I really didn't care for cunnilingus all that much, but I did my best to learn everything I could because Jenny liked it so much. The upshot was that by the end of the school year, I had become an expert in all the ways to please a woman sexually that Jenny could teach me. I did it because I wanted to keep Jenny happy. Of course, I enjoyed most of it, too.

That summer, Jenny announced that she was not currently interested in attending college. She wanted a career as a beautician, since she thoroughly enjoyed doing that sort of thing with her friends. Toward the end of the school year, Jenny started looking around for a summer job. Fortunately, she found a starting position in the salon that was most favored by the high school crowd. This gave her plenty of time to associate with her friends and to learn the business. Because she was not yet 18 years old, she could not be employed as a full-time worker, so she had her afternoons free to fuck with me.

Nobody wanted to hire me as a regular summer worker because of my age. Therefore, I made a few dollars here and there with lawn work around our neighborhood. As it turned out, Mrs. Ruth Jackson hired me more often than I thought was necessary to work in her rather large yard. Her husband traveled very often in his business, and many of those trips meant that he was absent from home for a few days, sometimes a whole week.

This turned out to be a very hot summer, so I often worked on a lawn dressed only in shorts and working boots. As I said, I was very buff and well tanned, so I was eye candy for the lonely women of the neighborhood. The result was that I never lacked for a job tending lawns during that whole summer. However, that was when I was introduced to my future vocation.

One morning, I was working in Mrs. Jackson's yard when she called me from the kitchen to come in for a lemonade. That was something new, but the weather was damned hot and the cold lemonade was a welcome attraction. What I wasn't expecting was how cold the air-conditioning was set, and it was not more than a minute or two before I started to shiver.

Of course I was covered with sweat and the dry air of the air-conditioned house made that evaporate very quickly. When the cooling effect of the evaporating sweat was added to the already cold air on my bare skin, there was nothing that I could do but shake. Mrs. Jackson acted very upset for my sudden chill, and I was inclined to agree with her. I very rarely got sick, and I sure did not want to catch a cold.

Before I could react any other way, Mrs. Jackson was pushing me towards the shower so that I could get some warm water running over my body. I was so deeply into my chill by then that I really was not competent to make many decisions of my own. Mrs. Jackson pushed me into the bathroom and closed the door. She turned on the hot water in the shower to let it warm up. In my stupor, I just stood there, not doing anything.

Mrs. Jackson pushed me down on the toilet and pulled my boots and socks off. She then had me stand up and, to my surprise, pulled my shorts and underwear off. I just stood there until she ordered me to step out of my pants and into the shower. I was still shivering like mad and barely aware of what was going on. I think Mrs. Jackson really panicked at that point because she quickly undressed and got into the shower with me.

At this point, I was barely aware that I was in the shower with a naked woman. Somehow, in my blurred mental condition, I confused Mrs. Jackson with Jenny. I guess in my confusion, I did what I automatically did when Jenny and I shared the shower: I reached for her tits. Without thinking, I began to fondle Mrs. Jackson's tits.

Her reaction was not what you would expect: she did not scream or push me away or anything like that! Instead, Mrs. Jackson began to moan in pleasure. I must have gotten enough hot water on me by this time to get my brain back into operation. I had stopped shivering and was enjoying the feeling of the warm water pouring over my body. Then it registered what I was doing to Mrs. Jackson's tits.

Naturally, as soon as I realized that I was in the shower with a naked woman whom I had never before seen without her clothes, my cock rapidly began to get hard. As I had said, I have a 7 incher, and the head of my cock pushed against Mrs. Jackson's pussy. She wasn't shaved down there, so I felt her hair tickle the end of my cock as I unthinkingly pressed it against her.

Well, I was still a little slow in my reaction time, so I just stood there and enjoyed the contact with Mrs. Jackson. If anything, she began to moan louder, and she reached down to grasp my extended cock in her hand. I must have moved just right to suggest it to her, because she began to move her hand as if she were jacking me off. What do you think a teenage boy would do under those circumstances? Well, what I did was to come. I sprayed jizz all over Mrs. Jackson's pussy and thighs, and I couldn't seem to stop. She began to shake, and I am convinced that she had a minor orgasm when she felt the jizz hit her.

She came down from her sexual high and seemed finally to realize what had happened. She turned off the water and pushed my hands away from her tits. Using my cock as a leash, she led me out of the shower and dried us both off with the same bath sheet. My cock had only decompressed a little as a result of her touching me in so many interesting places as she dried me. Therefore, it was still sticking out in a convenient position for her to grab and to lead me to the bed.

Mrs. Jackson was still carrying the bath sheet, and she spread it on the bed to act as a barrier before she lay down on it. I had regained my senses and recognized what Mrs. Jackson had in mind. Man, you can believe that I was ready to cooperate! Fortunately, I remembered practically all that Jenny had taught me, so I was ready to fuck.

The first thing I did was to lean over and give Mrs. Jackson a deep French kiss. She responded to my kiss and put her arms around my neck and shoulders. As I continued to kiss her, she pulled me onto the bed between her legs. We kissed for a few more minutes, and then I moved down to kiss her nipples. Mrs. Jackson acted as if this were completely unexpected, and she began to bounce her hips. I took that as an invitation and pushed my cock against her pussy lips.

Of course, she did not object and spread her legs even more for me. Her bush was so thick that I could not see her pussy lips. I reached down to move my cock head between her lips, assuming that I didn't have to see what I was doing to do the job correctly. I got a surprise when I had to move so near to the bed to find her pussy hole. Dammit, it was just too near the mattress for me to do a decent job of fucking. In a flash, I remembered one of the positions that Jenny and I had practiced.

I moved her ankles to my shoulders and that swiveled her hips and pussy up enough for me to get an easy alignment with her hole. I was able to push nearly straight down to penetrate Mrs. Jackson's cunt, and she sighed with delight as I slipped past her pussy lips. Mrs. Jackson was so wet inside and she was at such a good angle that it only took two strokes for me to bottom out inside her cunt.

Mrs. Jackson had such a deep hole that I never touched her cervix as I went in as deep as possible. I banged my pubic bone against her clit, and she acted as if that had never happened to her before. She squealed in delight and pushed back against me to get more pressure against her clit. "Oh, Billy, I hope you can do that again. That really felt good, and I've never had it happen before."

If that were the case, I wondered who she had been fucking. Obviously, it was a man or men who really didn't care what she felt. I was disgusted with her partners who had so little regard for her feelings. Well, I was about to show her what a caring partner could do for her. I said, "I will try to do that every time, if that is what you want."

"Oh, please do! That felt so good."

With that as a guide, I began to take full strokes into Mrs. Jackson's cunt, and I made sure to bump her clit at the bottom very stroke. With the way she was carrying on, panting and moaning, I figured I must also be rubbing her G-spot with every stroke.

At this stage in my development, I believed that there was no such thing as a bad fuck. This fuck did not compare in pleasure to those that Jenny and I had, but there was no question that I was enjoying it. Mrs. Jackson continued to pant and moan as I continued to stroke. Finally, I felt her begin to tighten up in preparation for an orgasm. This was enough to bring me along, and we came together. I was startled when Mrs. Jackson screamed in pleasure. Oh, well, there was no one to hear us, so it made no difference.

I considered it pleasant enough and an entirely adequate fuck from my point of view, but Mrs. Jackson must have looked at it from an entirely different angle. She grabbed me for a deep French kiss and began to cry. This was something totally unexpected, and I said, "Please don't cry, Mrs. Jackson. I didn't mean to hurt you! What did I do wrong?"

"Oh, Billy, you did nothing wrong. I am crying because that was the best fuck I ever had. Do you think you could do that again another time?"

"Oh, sure, Mrs. Jackson. I would be happy for a repeat performance whenever you are ready." We got up and dressed, but let me tell you, it was torture putting those sweaty clothes back on. Of course, I had not finished mowing the grass in the backyard, and I had to finish that before I got paid.

I finished cutting the grass and went back to see Mrs. Jackson about claiming the $20 he owed me for the lawn work. To my surprise, she handed me $120. I said, "Mrs. Jackson, I think you over paid me. What did I do to earn the extra money?"

"Just consider that extra $100 as a tip for your good service."

I thanked her and went home with the proverbial song in my heart.

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