How I Became a Gigolo - Cover

How I Became a Gigolo

Copyright© 2013 by aubie56

Chapter 8

Erotica Sex Story: Chapter 8 - 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  

Ruth Jackson arranged with Jenny for me to visit her on Friday morning. I confess to being excited by the thought of fucking Ruth Jackson again. She was so appreciative of my efforts that it was a big boost to my ego each time I fucked her. I was all cleaned up and dressed in my best summer casual clothes when I knocked on her front door at precisely 9:30 Friday morning.

Ruth must have been waiting for me just inside the front door, because she opened the door, grabbed me by the arm, pulled me inside, and closed and locked the door all so fast that she almost left my head spinning. Well, I recovered so fast that I doubt that Ruth noticed any pause before I embraced her and opened our session with a deep French kiss. This time, Ruth was startled, but she quickly joined me in initiating the session.

After about 15 seconds of kissing, Ruth pushed me far enough away so that she could regain her balance. She took me by the hand and led me directly to the bedroom. There was nothing coy about Ruth this morning: she knew exactly what she wanted.

She marched me directly to her bed and dropped my hand. Ruth was wearing a light summer dress that fell to the floor with hardly more than a shrug of her shoulders. She kicked off her slippers and faced me while wearing nothing but a smile of anticipation. "Out of those clothes right away! I can't wait any longer for you to eat my pussy!"

Well, there was no mistaking how anxious she was, so I removed my clothing and dropped them on the floor beside the bed. Meanwhile, Ruth lay down on the bed and spread her legs. I could tell that she had recently shaved her pussy in expectation of what I was going to do for her. I knelt between her legs and leaned down to kiss her pussy lips. Ruth couldn't help it: the moment, I made contact with her pussy, she let out a small scream of delight. That was what I wanted to hear!

I started work immediately on her pussy by licking her lips, first the right and then the left one alternately from the bottom to the top, but avoiding her clit. I gave her 10 strokes on each lip before I pushed my tongue just a little way into her pussy slit. I moved up the slit, but stopped just before I reached her clit and returned to the bottom of her slit to repeat the maneuver. I was only able to get in five strokes like this before she bounced her hips so much that I could no longer control the amount of penetration I was giving her with my tongue.

There was no question that I had Ruth's complete attention, so I grabbed her hips to hold her steady while I tried to continue licking her slit. This was totally impossible! Ruth just could not remain still, and she persisted in bouncing out of my hands. As a last resort, I backed off and pushed her legs so that her knees got very close to her shoulders; I was careful not to push hard enough to hurt her. Without her feet pressing against the bed, there was no way that she could do her bouncing strongly enough to keep me from holding her steady.

I returned to licking inside her pussy slit. Each time, I pressed a little harder so that I went a little deeper into the slit. It wasn't long before I dragged the tip of my tongue over her vagina opening, and that elicited a loud scream from her. Obviously, she had never expected me to do that. Now that I had reached her tunnel of delight, I stopped moving my head and simply tried to penetrate her opening with my tongue. Naturally, I could not reach in very far, but I simulated as best I could a fucking motion with my tongue in lieu of my cock.

This, too, was a novel experience for Ruth, and she reacted as if she were actually being fucked by my cock. I could not reach as far as her G-spot with my tongue, but I did manage to induce a small orgasm that caused her whole body to shake in a kind of rapture. I kept my tongue poked into her vagina until she came down from the orgasm, and then I moved to attack her clit.

Previously, I had done little with my mouth on her clit, but this time, I made a major effort to bring her to a strong climax just from work on her clit. I grabbed her clit with my lips and applied the strongest vacuum that I could manage. I hoped to draw her clit a significant distance from its sheath, and then I would proceed to attack it in earnest.

Her clit was pulled far enough from its hood so that I had no trouble holding it out with my lips with a significant portion of it extending inside my mouth past my lips. I held her clit as tightly as I could with my lips while I flogged it with the tip of my tongue. This sent Ruth into a spasm of ecstasy, and I simply continued to flog her clit until I drove her to orgasm. As she started down from her peak, I bit gently on the tip of her clit with my teeth, and that was enough to make her explode into another orgasm.

I could see Ruth's face, and I had a moment of panic when I saw the grotesque shapes she was forcing her face into. At first, I was certain that I had seriously injured her because Ruth let go with another one of those piercing screams. However, I recognized the flavor of the scream as being one of pure pleasure, so my fear immediately went away. She now began to bounce her hips with so much vigor that I lost control of the situation and just backed off enough to let her return to normal.

I was amazed at how long Ruth's gyrations continued as she completed her orgasm. Subjectively, I felt that this orgasm must have run for 10 or 15 minutes, though I knew that was impossible. Nevertheless, Ruth certainly had gotten her money's worth from my efforts. All I did now, was to wait until she was ready to be fucked, so I laid down beside her and we cuddled for a few minutes.

"Billy, you must be in league with the Devil to be able to produce such feelings in me. I never thought that I could feel something like that! It must've been as near to heaven as I could ever hope to get in this life. Without a doubt, you are worth every penny that your visits cost. I would love to have you visit me every day, but an experience like that every day would surely kill me. My heart just couldn't stand it!"

"Ruth, I thank you for the compliment, but I must tell you that you inspire me to give you the best that I can offer. I just hope that I continue to have the opportunity to provide you with such things."

Ruth continued to complement me on the quality of my fucking for another 15 minutes or so. I could tell from the sound of her voice, though, that she had recovered enough that she was beginning to want to feel my cock inside her. I certainly was ready, so I brought up the subject, and Ruth agreed with enthusiasm that it was time for a royal fucking.

I asked Ruth if she wanted to try a different position, but she answered that she really enjoyed the quality of the feelings that she felt in the Butterfly position. Okay, that was my favorite position, so I had no intention of arguing with Ruth. She did ask me to swap towels because the one she was lying on was now so wet that it was distracting. Furthermore, she wanted to catch it before she wound up sleeping on a wet spot tonight. I had no trouble sympathizing with the wet spot aversion, so I swapped towels for her and dropped the wet one on the floor.

We got into position, and I slid all the way home with my initial push. That initial act of penetration was something special to me, and I kind of missed having to work my way in, but I understand how Ruth could be ready to accept me, all in one shot. In any case, Ruth was the client, so I was not about to make a negative comment at this point.

I did pause for a moment at full penetration to make sure that Ruth was not uncomfortable after accepting the whole of my cock. She insisted that she was ready, so I began to stroke. The first two or three strokes were relatively slow as I got myself properly oriented to rub on her G-spot, but I sped up and moved at the stroke rate that I thought was best for Ruth. She made no negative comments, and I figured that I had chosen correctly.

I wanted to give her several orgasms before I came, but I was concerned that her massive orgasm during the cunnilingus episode was going to get in the way of that. Well, I could only try my best. I stroked for nearly the full length of my cock in an effort to apply as much stimulation as possible to Ruth's G-spot. Of course, that banging on her clit every time I bottomed out definitely helped the situation.

I continued to stroke at what I thought was my best rate, and I was surprised to find that I did not feel the least bit tired. I really don't know how long I could have lasted if it became necessary, but I was sure that I could last at least 30 minutes at this stroke rate. Surely, that was long enough to provide several orgasms for Ruth.

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