Adventures of a male prostitute #1

Jake sat in the living room of his Vista, CA apartment. His mind was going over ways that he could make a living without working a typical 8 to 5 job. Jake was a surfer and he wanted to be able to head for the ocean any time that he heard that the surf was up. He had tried sales but he wasn’t very good at it and made very little money. After days of thinking he decided what he was going to try next. He carefully worded an ad to put on Craig’s List and on one adult dating website that had a check box that said yes or no about whether you were an escort so he knew that they did not object to his kind of ad. He had to word it carefully so people should understand what he was saying but the authorities would not think that they had to react to it. He finally came up with:

” 20-year-old male. Blond hair and blue eyes. Athletic 6’1″ and 175# firm body. Fun to be with and a good dancer and good kisser. Well hung and long lasting. I enjoy spending time with financially secure older women. E-mail me and let’s see if we would like to spend some time together. Local or I can travel if you make the arrangements. [email protected].”

Jake placed the ads and waited to see what would happen. It only took a couple of days before he got his first reply. It was from a woman in her mid forties who lived in an oceanfront home in La Jolla, just down the beach from one of the spots where Jake liked to surf.

“Hello surfstud. I saw your ad on-line and would be interested in having you be my date to a party that I have been invited to out on Catalina Island. It would be overnight. Interested? I am a 44-year-old woman with an oceanfront home in La Jolla. I’m still in good shape. I think you will be pleased. I can be very generous with my time and my affection and more. I’ll look forward to hearing from you. Will you please send me a picture? Monica.”

“Hi Monica. It is great to hear from you and I am very interested in spending some time with you. Here is my cell phone number. Give me a call and let’s talk about it. Here is my picture. Jake. 760-555-1234.” Jake sent a picture of him in his speedo swimsuit standing on the beach with his surfboard.

“Hi Jake, I really like your picture. I watch the surfers down on the beach and I have seen you down there. I admired you when I first saw you on the beach. Here is my picture. I’ll call you tomorrow about 3pm unless you write back and tell me not to. The party is in four days, next Friday night. We would go on Friday and come back on Saturday. Monica”

Jake looked at her picture. It was she in a low cut red formal dress, all fixed up like she was going to a party. Monica had a pretty nice figure and an attractive face. She had a big rack but Jake could see that her breasts did sag quite a bit. You could tell that she took good care of herself. Jake was sure that she was well off as all of those houses were worth at least a million dollars or more.

Jake had never dated an older woman but he was looking forward to doing this and he was sure that he could make her happy. He was pretty sure that if this happened, she would be looking for sex. Jake’s nine-inch cock was always up for the job. He had never had any complaints and he dated frequently. He loved both giving and receiving oral sex and he was good for at least three good fucks a night.

Promptly at three, Jake’s phone rang. Jake answered, “Hello.” “Jake?” “Yes.” “This is Monica. I’m calling to see if you decided that you want to go to the party on Catalina with me. It is a bunch of my old classmates and I would love to have them see me being escorted by a hansom young stud. My ex will be there too and he is living with some young slut now. I want to show him that he’s not the only one doing well with the opposite sex.” Jake replied, “Tell me the details.” “The party is at the casino and I have reserved a suite at one of the hotels. We’ll take the ferry over from Dana Point. Where do you live?” “I live in Vista.” “You could plan to meet me at the Oceanside Harbor.” “It sounds like it might be fun, Monica. What would you expect of me?” “Well Jake, Enjoy the party with me and let everyone know that you’re my boyfriend if they are interested. Then we will spend the night in our suite and if we are enjoying ourselves, you can fuck the shit out of me as much as you want. From your ad, I think you might be wanting more from me. What else would you want?” “Sounds good to me. You would pay all the expenses and I would like $300 for myself.” “That sounds good to me, Jake.