How I Became a Gigolo
Caution: This Erotica Sex Story contains strong sexual content, including mt/ft, mt/Fa, Consensual, Heterosexual, Humor, Incest, Brother, Sister, First, Oral Sex, Prostitution,
Desc: Erotica Sex Story: Chapter 1 - 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.
I must have started out my career as a teenage boy pretty much like 99.9% of the rest of the male population: I jacked-off five times or so a day. Some days I did it even more than five times, but I had to back off when I got sore lumps in my armpits. I don't remember where I ran across the information, but I read that too much jacking-off could make those sore lumps. Anyway, when I cut back on jacking-off, the sore lumps went away, so I guess the information had been correct.
I guess you could say that I had a normal family: a mother, a father, and a sister, Jenny, who was about three years older than me. Jenny was not what you would call a raving beauty, but she was damned nice looking. I noticed that about the time she started growing her boobs, but I was really too young to grasp the significance of those lumps.
I found out sort of accidentally that she was dating on the sly when she was 13, and I knew she was no virgin by the time she hit 16. I knew that because Jenny would bring boys into her bedroom when she thought nobody was home, but I was there one day.
The funny noises coming from her bedroom were too much of a temptation for me to resist, so I peeked in on her when I got the chance. At first, I did not understand what was going on, except that I could tell that Jenny and her visitor were being very physically active and really enjoying what they were doing. I got more information later when it dawned on me to hide in her closet just before Jenny and her boyfriend got to her bedroom.
It was fun to watch them strip each other because they were in such a hurry that they got in each other's way. Sometimes I had to work to keep from laughing out loud at their antics. I really liked watching that part of the show because it gave me a good chance to study Jenny's naked body, something I had never before had a chance to do. Man, that provided a lot of inspiration for my jack-off sessions. It was great to see Jenny like that because she shaved the hair between her legs, and I got to see her bare pussy.
Also, by this time, her boobs really were worth looking at. Currently, Jenny was wearing a B-cup bra (I knew because I checked her laundry), and she only needed it for modesty. There was absolutely no sag to her tits, and her nipples were centered in beautiful pink areolas. Jenny was neither fat or skinny, but seemed to me to have just the right amount of meat on her bones. Overall, I just loved to look at her.
Usually, at this stage of the proceedings, I got kind of distracted as I was heartily beating my meat, so I did not pay much attention to the two of them climbing onto her bed. By the time I had shot my first load and was able to devote my full attention to the sex on the bed, Jenny's boyfriend was already pumping away at her. Unfortunately, my angle was not the best, so I was not able to see his cock penetrating her pussy.
Oh, I had taken the usual Sex Ed class, so I knew in theory what was going on. On top of that, I had heard all of the usual bull shit from my male friends and acquaintances about how fucking was done. Nevertheless, I knew I was missing a lot by not being able to see Jenny and her boyfriend in action.
Anyway, I enjoyed about six months of this voyeurism, until one day, Jenny marched into my bedroom. Naturally, she did not knock on the door before she opened it, and she caught me lying on my bed jacking-off. The first words out of her mouth were, "My God, Billy, how often do you do that? I figured you were getting enough from spying on me while I fucked in my bedroom. You were not very careful, so I found where you had dribbled jizz on the floor when you came."
I had snatched a pillow to cover my cock and balls, but Jenny had had plenty of time to see what I was doing. "God damn it, Jenny! How many times have I told you to knock before coming in my room? I always knock before entering your room, don't I?"
"Yeah, that may be, but I don't spy on you from your closet."
Well, she had me there. Not having a good comeback, I had the sense not to say anything. That probably saved my bacon.
Jenny said, "You never did answer my question. How often do you beat your meat?"
Well, she had me, and I knew I would not get any peace until I answered her question. "I usually do it around five times a day if I get that much time alone. Why do you ask?"
"We girls were talking one day about the size of a boy's cock and comparing what we had heard about the size among the boys at school. During the conversation, Mary Ashton said that she heard that you had the biggest cock in the freshman class. I got to thinking about that and about you watching me fuck, so I decided to check you out. Now that I have seen your hard on, I can believe what Mary said."
"Yeah, I guess that is true. I think I have seen most of the cocks in my class during the shower after gym, and I probably agree with you. So why this sudden interest in the size of my cock?"
"The truth is, I have gotten kind of bored with the fucking I have been getting from the tiny cocks of the boys in my class. Now that I have seen yours, I am anxious to give you a ride to see if you feel as good as you look."
"Jesus, Jenny! We can't do that! That would be incest, and that's against the law."
"Hell, Billy, that won't make any difference if you don't make me pregnant. I have been on the Pill for the past year, so there is no way that you could knock me up. Under those conditions, I can't see that the question of incest has any bearing on the matter! What I want to know is will you fuck me?"
"Dammit, Jenny, I'd fuck you in a minute anytime that I got the chance. Just tell me when and I'll be there! There is one thing you have to know, though: I am still a virgin, so you will have to teach me what to do."
"WHAT?! You took the Sex Ed course and watched me fuck I have forgotten how many times, and you are still not sure what to do?! Dammit, Billy, I know you're smarter than that!"
"Calm down, Jenny. Yeah, I know the general principles, but never could see you and your boyfriend clearly enough to know exactly what you were doing. Hell, I figured that you would have fun teaching me how to be a good fucker. I know you have had a lot of practice, so you ought to be the best teacher that I could find."
"Okay, Billy, you made the sale. Come to my room tomorrow while our folks are away from the house, and we will do our first session. I said 'first session' because you will need some practice before you can satisfy me completely. We'll start tomorrow and see how things go from there. It's a good thing tomorrow is Saturday, and we will have most of the day to ourselves."
Dammit, I had a hell of a time staying calm and not tipping off to our parents that something unusual was up. I did manage to keep the secret, so Dad left to play golf and hang out with his friends the rest of the day, and Mom left to meet her friends at the mall. We could figure that neither one would show up back at the house before 3:00 PM. That should be plenty of time for our first session of sex.
I wasn't sure exactly what Jenny expected of me, so I wore some boxer shorts and nothing else to her bedroom a few minutes after Mom left for the mall. I am pretty buff, so I was surprised when I walked in on Jenny and she giggled. Dammit, that was embarrassing, especially since she was naked as she lay in bed.
I blushed, and I swear it felt like it was from head to toe. I asked, "Dammit, Jenny, why did you laugh at me?"
"Oh, Billy, I was not laughing at you. You just reminded me of every porno film and video that I have ever seen when the hero first goes into the heroine's bedroom. I just thought of the connection between what we were about to do and the average porno. I'm sorry, and I promise not to do something like that again. Now shuck those boxers and join me in bed. I can hardly wait to feel your cock inside me."
Well, I got over my embarrassment damned quick and pulled off my shorts. Jenny was lying on one side of the bed and I crawled into the empty space beside her. She said, "The first thing we will do is make sure that you know how to kiss. Come over here closer and we will get started."
I had been kissing all my life, and I couldn't figure out why she would say I didn't know how to kiss. It didn't take me long to find the answer to that question. It was embarrassing again when I had to admit that she was right about me not knowing how to kiss a girl. However, I am usually a quick learner, so Jenny pronounced me to be an adequate kisser, and I learned the basics in less than half an hour. I advanced as far as being a decent French kisser quickly enough for us to go on to the next stage.
Naturally, by this time, my cock was as hard as it was going to get. At this stage, I was about 7 inches long and about 2 inches in diameter. Jenny took one look at it and said, "Dammit, I can't wait any longer. Get between my legs, and let's eliminate your virginity curse."
Of course, I was all for that, so I was between her legs almost too fast for her to see me move. Yeah, I knew on general principles where my cock was supposed to go, but the Sex Ed class had suddenly gotten very oldmaidish and very stingy with details. In other words, I really didn't know where to find her vagina opening, so I had to ask for help.
The first thing Jenny did was to spread her pussy lips with the fingers of her left hand and point out her hole with the fingers of her right hand. She also got smart and used her right hand to guide my cock head into position. She moved my cock head up and down in her pussy slit to get some lubricating oil on it; at least that's the way she explained it.
Once I was lined up, she told me how to push my cock inside her. I was careful not to move too fast and to give her time to adjust to my size. She had been adamant about that because mine was the largest cock ever to penetrate her. It took five strokes for me to penetrate her all the way. I felt my cock head bump against the end of her tunnel just beyond her cervix as my pubic bone struck her clit. She squealed at the combination of pleasure and pain, and I was not sure how to react so I just froze in position.
Jenny said, "Don't worry about it, Billy. I expect that I will stretch a little bit after a few fucks with you and enjoy having you bang my clit while we fuck. But for now, I'll have to ask you not to penetrate quite so far. I'll tell you when the situation changes."
If I had not been plugged into Jenny, I would have jumped for joy: I was no longer a VIRGIN! The feeling of her cunt fully enveloping my cock was impossibly great and thrilling! I felt sort of like I was fully enclosed in a velvet glove that was exerting pressure over all the right places. I wanted this feeling to stay with me forever, but I knew I would never be so lucky.
At Jenny's command, I pulled back out for almost my full length and pushed back in almost all the way. I wanted to make sure that this experience was not painful for her because I wanted to be invited back. Jenny said, "Oh, my God! You are rubbing on my G-spot, and that feels so good that I can hardly stand it. Billy, I swear that your cock is every girl's dream! I know all too well that it is not possible, but I wish you could stay there and fuck me forever."
At first, I moved slowly with my strokes so that I would not go too far in either direction. I didn't want to hurt Jenny at the bottom of the stroke, and I did not want to lose contact by pulling out of her cunt at the top of my stroke. Dammit, I had a lot to learn, and I wanted to learn it as fast as possible.
After a few of the slow strokes, Jenny had me speed up. That seemed to make a tremendous difference for her, and it sure did for me. Man, fucking must be the best feeling in the world! Uh-oh, I was about to come, and there was no way to stop it. I told Jenny what was about to happen, and she said, "Go ahead, Billy. I know how hard it is for you to hold back on your first time. Just go ahead and shoot, and we will do this again in a few minutes, as soon as you can get hard again. I don't expect to come this time, but I know I will the next time."
I only managed four more strokes before I came. I felt like I was shooting gallons of jizz. Jenny felt me shooting, and that was what was needed to trigger her orgasm. She started panting hard, and her face screwed up like she was in tremendous pain. I had never seen her react like this when her boyfriends fucked her, and I was scared that I had hurt her. I froze, not knowing what to do, but I continued to squirt at least three more jets into her cunt before I was finished.
Jenny just kept coming, and I don't know how long it was before that crazy look left her face. Whenever it was, she looked at me with complete adoration in her eyes and pulled my face down for a kiss that seemed to express complete surrender. I asked, "Jenny, did I hurt you?"
"No, Billy, you did not hurt me! You gave me the best come that I have ever experienced. If you can keep that up, I will never fuck another man as long as we both live. I can't wait to thank Mary Ashton for clueing me in! You must have the best cock in the whole city, and I'm the only one who knows that. Maybe I won't say anything to Mary after all. I wonder if it would be fair to my friends to keep you for myself?"
I didn't know what to make of Jenny's rambling talk, but I did remember the last part, especially. Jenny had been so good a fuck that all I was interested in at the moment was getting a repeat run with her. At the moment I was so limber that my cock was just flopping around. It did not reduce in length enough to notice, but it did shrink in diameter down to a little more than an inch and a half. That was still a little larger than I was used to, but the change meant nothing to me at the moment.
Jenny and I cuddled for about 20 minutes before my cock started to get hard again. I guess I was about half-hard when Jenny looked down at it and said, "Billy, can I try an experiment?"
I had no idea what she had in mind but I said, "Sure, go ahead."
The next thing I knew, Jenny had swiveled around in the bed, and had taken my cock into her mouth. Like everything else on this day, this was my first time for having my cock in any girl's mouth. I think my cock hardened to its full capacity in only moments. My cock had been exposed to the open air long enough for the body fluids to begin to dry on it. I can't imagine what the crusty feel must have been like, but Jenny did not pause before she had as much of my cock as possible inserted into her mouth. Oh, my God! That felt almost as good as fucking!
The only way I can describe what happened was to say that Jenny acted as if she were trying to fuck my cock with her mouth. Fortunately, she stopped before I came again, and I suppose that was her plan. She released my cock and swiveled back around to give me a deep French kiss. Now I knew what my used cock tasted like: it wasn't so bad, but it was not a taste that I would relish. On the other hand, Jenny seemed to like it. Well, I sure as hell didn't care as long as Jenny was happy.