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. firstname.lastname@example.org."
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. It's a date." I'll be driving a red Mercedes SLK. I'll pick you up by the first restaurant in the harbor at eleven on Friday morning. It's formal but not Tuxes so just bring a nice suit." "Done. Call or e-mail me if anything comes up in the mean time or if you just want to talk." "OK, Jake. See you then. Bye."
Jake hung up and thought how smoothly that went. Was he really going to get paid for doing what he liked most anyway? He probably would have gone for free if he had met her in a different way. She was older but attractive and he thought it should still be enjoyable. The next few days passed slowly. Thursday morning there was an e-mail waiting for Jake when he got up. "Hi Jake. Everything is still on schedule. Are you ready to meet me tomorrow? I'm really looking forward to it. I'm especially looking forward to our time after the party. Monica." She attached a photo of her in a fairly small two-piece swimsuit. "Not bad," Jake thought. "He e-mailed her back and said that he was looking forward to it.
Friday morning Jake was waiting for Monica. He was dressed in tight shorts and an even tighter tee shirt that showed off his muscles. He had a small suitcase with his suit for the party, a change of underwear and a swimsuit in case there was a hot tub or they went to the beach. He had thought about stopping at the drug store to buy some condoms but decided that if she wanted to use them, she would have to bring them. He had no desire to use them. Monica pulled up in her red SLK wearing a red sundress. "You really like red." "Hop in stud." Jake got in and Monica leaned over and gave him a kiss. Her tongue was the first to enter the other's mouth. Monica reached over and gave Jake's package a squeeze. "Nice." was all she said. They left to catch the ferry. On the ride up they made mostly small talk but Monica also handed Jake an envelope." "This is for you." He knew it was his three hundred dollars. He tucked it in his pants pocket without opening it. "Thanks."
On the ferry ride over to the island, they spent a lot of time standing at the rail. Jake stood behind her with his hands around her on the rail and pressed his cock against her ass. Monica wiggled her ass back against him. They could see people looking at them but neither of them cared. Jake asked Monica how she liked to be treated and she told him, "Romantically but firmly." They got to the island at three. The hotel was walking distance from the ferry landing but they decided to rent a golf cart, which is the primary way people get around the town area on the island. On the way she asked him if he wanted her to give him the money so it did not look like she was paying. "That's OK. I don't mind." Monica checked them in and paid with her credit card. They went to the room. It was very nice and had an ocean view.
"We have about three hours before we go to the party. Dinner will be served there so we don't need to eat first. What would you like to do?" Monica asked. "They have a spa. Lets take a soak" Jake replied. Without another word, Monica stripped out of her sundress, panties and bra. Jake was right behind her. Jake looked at her. She was about 5'6" and her measurements were probably 42-D - 30 - 38. Her tits did hang down but they were still nice and she had big nipples that were already hard. Her muff wasn't shaved but it was nicely trimmed. Her mound stuck out with fat pussy lips. Jake knew that it was going to be fun eating and fucking her. Monica looked at Jakes sculptured body and stared at his package. He was about seven inches soft. She looked longingly into his eyes. "Monica, you don't have to wait till after the party. Why don't you go ahead and suck me now."
Monica dropped to her knees in front of him, reached out and took Jake's manhood in her hand and guided it to her mouth. In less than a minute she had him fully hard. Now she could hardly get her hand all the way around it. She pulled away and just admired the magnificent cock in front of her face. She stretched her jaw wide to get his cockhead back in her mouth. Stroking his shaft with her hand while she sucked and licked the head, she serviced this true stud that she had hired to be her escort. Pulling off again she looked up at him and said, "Don't just stand there Jake, go ahead and fuck my face. Make me take your wonderful cock and make me swallow your cum. Jake put his hands behind her head and held her in place as he started slowly pistoning himself into her mouth. Monica sucked as hard as she could. She was taking about half of Jake each time. If he tried to go deeper she would gag and interrupt the rhythm. Jake stopped trying to go deeper but just picked up his speed.
Jake pumped her face for about five minutes. Monica's jaw was starting to get sore and she was thinking she might have to give up when Jake froze and groaned. Monica felt his shaft pulse between her lips as Jake blasted shot after shot of his hot, thick, and salty cum into her mouth. Monica swallowed about half of it and held the other half in her mouth. She pulled off his prick and looked up with her mouth open showing him the cum that she still held in her mouth. Then she swallowed the remaining spunk, licked her lips and stood up. Jake kissed her and told her how great of a cocksucker she was. Actually he was thinking that he had had better many times.
Then Jake took her and almost threw her on the bed and climbed on with her. "Time to return the favor. Spread your legs." Jake dove for her muff. Monica was soaking wet. He ran his tongue up and down her slit, sucked and gently bit her clit and buried his tongue as deeply into her fuck hole as he could, bringing Monica to a hard orgasm. She pulled her head up and said, "Fuck me now, Jake. I want your cock in my cunt. Fuck me." Jake calmly told her "No. That can wait till after the party." Then he ate her till she came again. "Let’s go to the spa now. As they walked to the spa they drew more looks from other guests. Monica had her arm around Jake's waist but as they walked by, one person half jokingly asked "is that your son?"
When they got back to the room it was time to get ready for the party. Jake put on his suit and Monica did her hair and makeup and put on her dress. It was the same red dress that was in the picture she had sent him. Being summer, it was still light when they went out and the weather was in the low seventies with a light on shore breeze. Monica brought a light white sweater thinking that it would get cooler later. They got in the cart and drove to the casino.
The party went just as well as Monica had hoped. Although several others were also with new and younger partners, Jake was probably the most hansom person at the party. Monica was especially happy when she saw that her ex's new young girlfriend was a little chubby and plain looking. She made sure to introduce Jake to her ex. Jake turned out to be a very good dancer and Monica danced almost every dance, either with old friends or with Jake. Jake was very attentive and romantic, taking several opportunities to give Monica a big deep kiss, always when there were others around to see them kiss. The party started to break up about ten thirty. The only people who stayed were the one that were intent on drinking too much. Jake and Monica had each only had a couple of drinks.
Jake had put a blanket in the cart, telling Monica it was in case she got cold. When they left the party, Jake drove the cart in the direction away from the casino. He knew the island fairly well and knew a path that took them along the beach away from town. After a few minutes they arrived at an isolated spot and Jake stopped the cart, took the blanket and spread it on the beach. He helped Monica out of the cart and onto the blanket. The moon was nearly full and they watched it over the ocean.
Jake started kissing the back of Monica's neck and fondling her tits. "Let's get you out of that pretty dress." As soon as Monica was naked and laying on the blanket, Jake stripped out of his clothes and lay down with her. He kissed all over her body and had her moaning loudly. "Yes Jake, that feels so good. Don't ever stop." Jake rolled between her legs and gently slid his cock into her very wet and ready cunt. He slowly stroked himself into her and gradually picked up speed. His large size filled Monica to the fullest and she was starting to go crazy, moaning and rolling her head from side to side and gripping the blanket. "Yes Jake, that feels soooo good. Fuck me hard. Fill me with you seed.'' Jake lasted for almost fifteen minutes before he came. Monica had three strong orgasms while he fucked her. Finally he shot his wad. He stayed in her for another minute or so then pulled out. Monica quickly turned and sucked Jake's cum covered cock clean. They didn’t realize that they had stopped close to the Boy Scout camp and that two young Boy Scouts had been behind a rock watching them all the time they were there. Jake put his pants back on and helped Monica with her dress but she did not bother putting her panties or bra back on. Actually they could not find her panties and left without them. After they left the scouts spotted the panties and rushed out and got them, then headed back to camp to tell their friends what had just happened and show them their prize as proof.
On the way back to the hotel, Jake kissed her passionately several times and told her that by the time they got back he would be ready for more. Her reply was "Me too. Me too." Back in the room they both stripped and shared a shower, washing off the sand and sweat. Jake loved showering with his dates. The touching and rubbing with the slippery soap felt really good. Monica showed that she liked it a lot also. She cleaned his cock better than he ever had himself. After drying, they jumped into the bed and Monica headed for Jake's cock. After a short 69 suck session, Jake put Monica on her hands and knees and entered her from the back doggie style. While fucking her cunt, he touched his finger to her ass hole and started playing with it. When he tried to push it up her shitter. She stopped him and told him that she did not like anal and asked him not to do it. Jake thought to himself, "She's paying for this so that's her choice." He left her ass hole alone. After almost fifteen minutes of fucking his large manhood into Monica, Jake came again. Without even pausing, Monica went down and cleaned him. She looked at Jake. "I'm sorry but I'm really tired. Can we go to sleep?" "I can go again if you want but if you're done for the night it's OK." Monica cuddled his back, pressing her large tits against him and reaching a hand over him and holding his cock as she fell asleep.
The next morning Jake woke her up by announcing that breakfast was here. He had ordered room service and signed to the room bill. Monica smiled and sat up. That was when she realized that she had been naked on top of the sheets and that the bellboy must have seen her there when he delivered the food. Jake was just in his boxers and they had a big tent in the front. After eating, Jake put the trays aside and pushed Monica flat on her bed. He gave her a deep French kiss and then kissed her breasts. Then he moved to her belly and ran his tongue around her bellybutton. He continued his kissing down to her mound and kept going all the way to her feet. After sucking each toe, he worked his way back up to her crotch and proceeded to eat her to another climax. Lastly, in the missionary position he gave her a slow fucking, lasting so long that she thought she should tell him that she was ready and he should get on with it. Finally, before she did, he filled her again, making her come at the same time. He was again rewarded with a wonderful cleaning. Monica loved sucking a cum covered cock.
They had about three hours before the ferry left to go on its return trip to the mainland. "What should we do?" asked Jake. "Let’s just walk around town like tourists. They turned in the cart and spent the rest of the time hand in hand, looking in shops and eating lunch. On the ride back, they spent a lot of time at the rail just like on the way out but this time Jake was kissing the back of Monica’s neck most of the time. Giving her chills all over her body. After landing they drove back to the Oceanside harbor to Jake's car. Rather than going directly to it, Monica parked in an empty corner of the lot, pulled up the armrest between the seats and gave Jake one last blowjob. "You were wonderful, Jake and I think your you enjoyed yourself too." "Yes I did." "Be sure that I’ll be calling you again, Jake." "Please do. I'll look forward to it." Monica put another hundred dollar bill in Jake’s shirt pocket and drove over to where Jake's car was parked and he got out. Monica waved and blew him a kiss as she drove away.
A couple days later, Jake opened another e-mail. "Hi Jake, my name is Alice. I'm a friend of Monica. She told me about last weekend. I live in Denver. I'm going on a two-week trip to Europe but my husband can't go. How much would you charge me to go with me? I've enclosed a picture of me and I hope to hear back from you. Hugs, kisses and much more, Alice." Jake opened the attached picture. Alice looked a few years older than Monica. She was thin with small tits but attractive. The picture was of her, naked on the bed fucking herself with a big bright red dildo. She had written a caption on it that said, "I like red too, just like Monica." Jake got ready to write her back a very sexy e-mail accepting her invitation and telling her his terms.