stdlvr69
11-27-2013, 07:46 AM
I guess I should give a little background. I am married and have a loving husband and three wonderful children. I was on a long weekend and decided to travel to visit my brother who lived a couple of hours away. I had not heard from my brother in about a month and a half and I was beginning to worry about him since we usually chatted at least once a week and frequent emails. I decided to surprise him with a visit. Little did I know then that it was going to be me who was in for the surprise and a shocking change to my quiet life.
I arrived on Friday evening and the door was open so I went in. I was shocked to see my brother tied to the kitchen chair with his hands behind his back and feet tied to the legs of the chair and a man repeatedly punching him in the face. My brother looked terrible. His face was all swollen and blood was coming out of the many cuts all over his face and nose. I thought he was going to die and I started screaming at him to stop it and I yelled I was calling the cops.
The man was across the room faster than I could react and before I realized it he had taken my cell phone and had me in some kind of hold with my arm behind my back and I had to keep standing on my top toes to keep the pain down. The man looked at my brother and then at me and said maybe your pretty girlfriend would be willing to work off your debt this weekend and if she does I will not break both your arms and legs. My brother looked terrified as the man spoke and then looked at me with the same terrified look on his face.
The man asked me my name and I said Eve. He said well Eve you have a very nice face and I think under that baggy sweat shirt you may even have a nice body to go with it. He said he was going to give me a choice. He said I could stay and watch him break both arms and legs of my brother and he would be satisfied for a while that that was an interest payment on the money Bo owed the loan shark, or I could work it off for him and his debt would be paid if I cooperated and was any good at satisfying his customers.
I said what kind of customers and he said mostly married men who do not get enough at home and are looking for some fun. I realized he was talking about sex and using me as a prostitute to get the money my brother owed him. My brother had since passed out from the beating he already received and was not saying anything. I asked how long and what type of guarantee I would have that he would not renege on our deal. I said I had only briefly known him – my brother, but I might be willing to help him out if I had some guarantees.
We had arranged a deal that I would work for him the rest of the weekend until Sunday at 5:00 P.M. and the debt would be clear and I was free to go and there would be no attempts to try to blackmail me or anything else. I was scared to death of what I was agreeing to and at the same time there was a certain excitement about having to have sex with strange men. I have been faithful to my husband for the past twenty years and had not really thought about cheating on him.
The loan shark said before he had the final agreement he needed to see how good I looked and if I could perform sexually. I was a bit squeamish at first and then I thought what the heck if I was going to do it with other complete strangers why worry about this guy now. He told me to undress and when I did he said I should not hide such a sexy body like that under all the baggy clothes I wore. I smiled and asked what he wanted me to do. He said for starters I want you to see if you can suck cock good enough. I said I thought that would be coming and he said yes. Then he surprised me and told me to suck Bo’s cock and make him cum even though he was passed out. He said if I could bet him to cum in a short amount of time he would know for certain that I would be good enough.
I was not really sure I could give my brother a blow job and make him cum. There were so many things running thru my head at the time. I did not really care to give a blow job and now I was going to give one to my brother – that was incest. I was thinking about it when the loan shark told me he was finished untying him and to get the show on the road. I went over and fumbled with his belt and after a few seconds I got it open and started working on unzipping his pants. I was trying to work on him when I looked up and there was the loan shark with a knife and then he cut the pants and underwear right off and said that ought to make it a little easier for you.
I spread his legs apart and took hold of his limp cock in one hand and began to stroke it a little and then I started to lick the head and suck it into my mouth. I was hoping Bo would not say anything to give me away or to make it more difficult. I got him hard faster than I expected and in a few seconds he was rocking his hips and grabbing at my head to go faster and to suck more into my mouth. I took it all the way into my mouth down to the base and sucked and licked him a little before I pulled back up and went down again and in another second he was cumming in my mouth. I opened my mouth to show the loan shark that he came and he said good job and put his cock in my mouth and said do me now too.
I took the load sharks cock into my mouth and licked the head and put my tongue into the tip of his cock and then sucked him all they way down and back up and did the same thing all over again. I played with his nuts stroking then and tickling his anus with my finger as I sucked him all the way back into my mouth. I thought of their sizes that neither of them was very long or fat. I thought of Bud and how he was and then compared and made a mental note the next time to pay more attention to his size. I was a bit surprised when the loan shark came so fast. I had cum dripping down my chin and looked up at him and asked if he was satisfied.
I was thinking about what I had just done in the matter of ten minutes I cheated two times on my husband with two men, of which one was my brother. I thought I found myself enjoying myself after getting over the initial revulsion of having sex with someone else and that I was actually looking forward to more. I was feeling rather wet at the time and hoped in one way they would not notice and in another way I hoped they would and one of them would eat my pussy and give me some hard cock and make me cum.
Bo was looking thru his swollen eyes and I knew he would not be able to eat my pussy, but he would be lucky to be able to get it up again after having had such beating. Bo surprised me that he was standing there with his hard cock pointing at me and he went over to me and spread my legs and began to rub his cock up and down my slit and then put the tip on my clit and rubbed it all around and told me he had dreamed about this for a long time and now I was really going to get it and he plunged all the way into my pussy. Bo was ready to cum when all of a sudden the loan shark burst out DO NOT CUM INSIDE HER!
Bo pulled out and shot his load all over the front of me. The loan shark said he had a special customer for me and I would work off half of my brother’s debt in the first job. He explained he had a older gentleman who wanted a mature woman to go out on a date with that did not look like a kid and he was willing to pay extra for the date and he had just described me to the man and he agreed to pay $2,000.00 for the night if I looked as good as I was described and maybe even a bonus.
Bo looked at the loan shark and said that was what he owed him. The loan shark explained cost and interest charges to him and if he in the mood for another beating he could arrange it. The loan shark also explained he had a deal with your girlfriend to work off your debt by working for me all weekend until 5:00 P.M. on Sunday. I agreed and said I had made the agreement but I did not realize I would make as much in one night as what was owed. The loan shark agreed that a deal was a deal and if I wanted to back out he could still break Bo’s arms and legs.
The loan shark said the first thing we need to do is to go shopping. You can not go out on a date in sweats and you will need to look very sexy. He said Frederick’s of Hollywood should due nicely and we left.
I was amazed that women would actually wear some of the clothes they sold there in public. I was looking a long evening gown that had a slit up one side to the top of the leg and a deep plunge down the middle and an open back. I looked at him and said you might as well almost go nude. He looked at me and with all seriousness said that is the whole idea. He told the girl he wanted one like I was looking at in my size to go.
I tried on a couple of them and the sales girl said she would have to have one altered for me as the two they had that had the right size one was too tight and would be very uncomfortable and the other was a bit looser on the top and would more than likely fall off if I was not careful. He said we would take the one that was too large and we would not wait. The sales woman said she could put a couple of darts in near the top so it would fit better. He was a bit impatient and said only if it does not take too long.
I figured she needed a little help and I asked where the lingerie was. The loan shark said that is a good idea and followed me and another sales woman to where they had all kinds of lingerie. He asked if I could try some on and she looked at me and then back to him and said timidly sure if she does not mind. He replied she does not mind. He picked out two and said try them on and let me see what you look like.
I went into the changing room and the one woman said he is quite demanding. I said I know and I will be glad when the week-end is over. She asked why and she was the only one who noticed I had a wedding ring on. I said I agreed to try anything until Sunday night in order to avoid a lot of pain and suffering. She said I was a saint and she would just let the asshole crash and burn.
I put on the first nightie a long sheer thing with spaghetti straps and a deep plunge. There was not much to it and if you move the straps it would fall to the floor. I thought of my husband and wondered why we even bothered it would only be on for a minute before they would have it off. I looked in the mirror and thought I would be walking out into he store practically nude and all the people would see me and would be able to see thru the thin material. I got a little excited at the thought of it.
I walked out from the dressing room and he was standing there talking to another man who was a bit older and his wife was looking at a nightie. His wife was a lot younger and he commented on how sexy I looked and called his wife to see also. I paraded around so they could all see and then went in and got on the other one, which was a short thing with a g-string. I did the same and he said he would take both and the other man and his wife were there looking like they were stunned.
The other man asked his wife to try one on and let him see how she looked in it and at the loan shark and said wait until you see her. I looked at her and she had the fear of God look on her face and I said it is not that bad – just do not look anyone in the face except your husband and you will be okay. Just think you are in the bedroom. It was actually very exciting for me knowing all the people could see me and the men would be excited by what they were seeing.
The loan shark said we would wait to see her as it would be rude to leave his new friend without someone to comment on the outfit too. I stood there watching too. She came out in the same long nightie I wore and she looked scared. I told her she looked great and to smile and she seemed to relax and smiled. The man said you look sexy enough to eat right here and any man would be proud to have you with him. It must have been what she needed because she looked for approval from the loan shark and asked what he thought.
The loan shark said he could get people who would be willing to pay to see her like that and they would love to share her in bed. The man smiled and said I told you that you looked great and you could be a great hooker if you wanted. She laughed and said what man would pay to have sex with me when there were hundreds and thousands of teenage hookers and other in their twenties who were younger and firmer than she was.
The loan shark looked at her husband and then who me and then to her and said I know hundreds of guys who want a date with a mature woman who would fulfill their fantasies. These men are older and more refined and are not looking for young they are looking for women like you and her pointing to me who are classy and respectable and would be acceptable in public. Then he added that the money is good also. You could earn $500.00 for the evening, plus tips if you were nice and gave her a wink and a smile and looked back at her husband. He pulled out a card that had his name on it and a modeling and escort service name on it and handed it to her husband. I would be available to help her pick out her outfits so she would look sexy and alluring, but not slutty. Then he pointed to me and said isn’t that right Eve. I replied yes.
She looked at me and asked if I was not married to him and I replied a little more emphatically No than necessary. I said I had a situation and needed a lot of money and could not wait and in the course of the weekend I would make that much money and my debts would be cleared. She looked at her husband and then back to the loan shark who for the first time said call me Buddy. She said how much money. Buddy looked at her and said I could get you $400.00 a night. The man said is that all night or just the evening.
Buddy explained that typically a job would start at 8:00 P.M. and would end at 1:00 A.M. and that it would last longer if the woman wanted it to last longer and then there would be bonus money involved and that would be negotiated directly between you and the person you are escorting. There are others who like starting at 9:00 P.M. or 10:00 P.M. and stay out until 2:00 A.M. to 3:00 A.M. Buddy said he only provided to service opportunity and they rest was up to them.
I was listening intently to the offer and what he was saying as I knew what was expected in the end. The woman’s husband Ralph asked how many weekends Carol would have to work if she wanted to work. Buddy said it was entirely voluntary and it was not always weekends and some times it could involve travel as he had a customer who wanted a date to go on a cruise to Alaska with him and he had a woman take him up on it.
Carol said if you were picking out an outfit for me what would you pick out. Buddy looked her over and we all went over to where the dresses where and got one that accentuated her waist line since her breast were not as large as mine and she had a nicer bottom. Carol had him pick out a second outfit and said just to see how you would have new dress.
Buddy picked out a long skirt and an adjustable wrap blouse that could be adjusted so she could choose how much cleavage she was going to show. Buddy commented some men are more interested in how sexy and alluring you look and some are more interested in how much of you they can see. This is an outfit you can do both. Ralph asked Carol to try it on and get our approval. I had the distinct feeling Ralph was going to ask Buddy when she could start working.
Carol went in and before she was all the way in the dressing room Ralph had asked all the particulars and if sex was required. Buddy said sex was not required but would be a plus if she was going to get a bonus and if she was going to have some regular clients who asked for her specifically. Buddy mentioned several women he had who were always busy with the same clients every time they came to town. Ralph asked if they were all from out of town or if there were any locals. Buddy said I call and tell you what I have and show you the pictures of the client and give you their likes and dislikes… Then you decide. Most escort services are $300.00 - $400.00 per night and some higher. Suppose a man who is not as appealing to be with in public wants a date and the girl decides she would go out with him if she got more money she could get more, but it would have to be agreeable to all parties involved. I have a girl Katie who will go out with fat men for $750.00 a night and a lot of the other girls will not do it at all. So Katie is always in high demand.
Carol came out and modeled the outfit for us and Ralph said you could be an escort looking like that. Buddy said I could get you a date tonight at one of the nicest restaurants in town. Carol looked at Ralph and then to Buddy and then to me and then said it would have to be later as they did not have the money to purchase all the clothes now. Buddy said I will take care of it as a gift if you are going to do this for me. They all agreed and Buddy said a limo would pick her up at 9:00 P.M. and have her back by 3:00 A.M. if it was acceptable to both. The all agreed.
Ralph asked when she would get paid for going out and Buddy said they are all paid in cash after each date. Carol asked about the bonuses and Buddy said they are paid to you directly by the client. What you do to get it and what you do with the money is your business. Buddy looked at me and said come on Eve you have work to do and that I was his new good luck charm.
I had taken all the things in that had just transpired in the past few hours and for some reason I was actually thinking about becoming an escort. I hated the job I was working at and we needed the extra money and since I would be paid in cash I would not have to report on taxes any of it. I was thinking about all the possibilities as we drive to Buddy’s office.
The office was in an upscale office complex and there was a lot of security and it appeared very professional. On the way into the elevator one very distinguished older man was getting out as we were getting in and he said hello to Buddy and then winked at me and asked Buddy if I was a new girl? Buddy replied a very selective one. The man answered looking at me that he would be willing to pay extra for a date with me. Buddy replied that Sunday was open until 5:00 P.M. and after that I was done for this week. He looked at me and then said double the normal rate and they agreed and he said have her ready for lunch at 11:00 A.M. at the marina and they would spend the afternoon on the yacht.
I looked at Buddy and did not say anything and then to the man and smiled and in the sexiest voice I said see you later.
We arrived in Buddies office and he told me to change into the evening gown as the other man who was interested in going out with me also worked in this building and he would be picking me up here. Buddy had gotten me a nice handbag to go with my gown a little large than normal so it would fit the nightie he got me. I was to take it with me as we would be coming back to the penthouse when we finished dinner and I would be needing to relax and have cocktails after we got back and since I was paying off my brothers debt I would be required to provide sexual services at not additional charge to the client.
I got dressed and waited very anxiously for him to arrive. Fred arrived promptly at 7:30 P.M. and was very mature looking. I thought he looked old enough to be my father. Fred commented on how sexy I looked and that he was glad I did not look like his granddaughter. Fred explained he hated going out to dinner with someone who looked like a child and not a date and how hard it was to get a sexy mature woman to have dinner with. He went on for a minute or two and then we left, after Buddy told him I had to be back first thing in the morning as I had another customer for lunch.
Fred looked at Buddy and asked if it was Bill? Buddy replied yes and smiled. Fred said he was always doing that and they would have to talk about Bill getting the same girls. Buddy said it was just business and Bill had met me in the elevator and what could I say when he said he was willing to pay double the going rate. Fred smiled and looked to me and said let’s go.
We went to the Victorian Manor for dinner and cocktails and Fred was positively beaming as a lot of older gentlemen and their wives were arriving for dinner and going thru the niceties. One of the men whispered something to him and he blushed and smiled and said maybe another time. One of the ladies said it was nice to see him getting out in public again since the loss of his wife and it was nice that he finally had someone more appropriate for a date than the little children he brought to dinner before. I looked at Fred and smiled and said it looks like I am a hit with some of your friends.
Fred ate very slowly for a man and half way thru dinner he asked if I could adjust my dress so he could see a little more cleavage. I smiled and adjusted the straps and asked how that was and he smiled ands said he was hoping for a bit more and mentioned to a woman a little older who was almost falling out of her top. I asked if I should just go topless. He said no, it would not be appropriate but a little more revealing would be nice and said it would influence his tip, but cautioned me on looking slutty.
I went to the ladies room and took off the gown in one of the stalls, which were very roomy for a restroom. I took the darts out of the sides of the dress so it would open more in the front and put it back on. I was looking in the mirror when I saw Carol coming in the restroom and asked how she was enjoying herself.
Carol smiled and said very nicely I just have to get rid of my panties as they are positively soaked. She quickly explained that shortly after they left Buddy called and said he had a date and gave Ralph $450.00 in cash as he picked me up and brought me here and introduced me to Bill. She explained Bill was a horny old goat and talked dirty to her when ever there was not anyone in ear shot. Carol said he offered her $100.00 each for her bra and panties and to come in and take them off and come out and give then to him at the table. Carol said Ralph would never know and besides he had to take Viagra to get it up and some times it did not work. Carol smiled and said I think if it goes right I am going to get lucky with Bill. I said make sure you do not do it for free. I could not believe what I had just said. We hugged and went our separate ways.
I apologized to Fred for taking so long, but I had to alter the dress to get the desired effect. Fred beamed and readily approved and said it was fantastic. Fred went on how sexy I was looking and how all the other men would be envious of him having such a hot date. I asked if all the men were not with their wives and Fred replied that most of them were widowers and only a few were married. Fred explained the two women who came over and introduced themselves to us were wives of the men they were with and the rest of the men were with dates.
I looked around and asked Fred if he had dated any of the other women there and he said yes, but none compared to me. I blushed and he said no really you will be a prize as you are more mature and have the look of being brought up properly, not like most of the young girls who are here now. I looked around and took a real good assessment of the women and had to agree most of them looked out of their element. I made several mental notes and then asked Fred if he like having a variety of women to go out with or just a few.
Fred said he had not found one until now that he would really consider going out with on a regular basis and this was sort of the proving grounds before going out to some of the other restaurants and events. Fred asked how I liked the theater and I said we are not talking about the movie theater I take it and he said no – Broadway. I replied I had never been there and he asked how I would like to go. I said it would be great, but not this week-end. Fred replied that he knew already and kind of got sad.
I told Fred I would have to make some special arrangements to go as it would require me to leave my regular job for a while. I told him I was not a regular girl working for Buddy even though he wanted me to be a regular. Fred said he could understand why at the price he charged for me. Fred said it is normally $750.00 per night for the girls and the young ones were expected to have sex with us. He said that sex was up to me and I would have to tip extra for it. I smiled and said I was glad to have that information. Fred looked like he let the cat out of the bag and got caught and then smiled and said only willing to help someone who I am hoping to see more of in the future.
I sat there thru the rest of dinner quietly eating and making sure I leaned over enough for Fred to get a good view and to look more proper when people came over and greeted us. By the time dinner was over Fred was the envy of most of the men in the place and a lot of the women also commented on how radiant I looked with Fred.
Fred paid the bill and we left. I was holding his arm and we were getting into the limo when another couple came over and commented on how nice we looked together and Fred smiled even more. The woman commented to me that I must be special as she had not seen Fred smile and look so happy in a long time. Then she said to Fred that he would have to bring me out to the house for dinner some time. Fred smiled and said we will see.
I looked up at the driver and Fred noticed and pressed a button and a dark glass came up and we could no long see the driver. Fred pressed another button and talked to the driver and told him to take the long way back to the penthouse and he was turning off the intercom.
Fred asked if I minded and leaned over and kissed me. A soft gentle kiss like that of a lover not someone trying to get laid by a hooker. Fred took his time kissing me and gently rubbing my back and shoulders. I could tell he was trying to get more of a view down my dress without being over obvious about it. I decided to help him and dropped my shoulder so the strap would fall easier as he rubbed my shoulder and back and I turned and did the same on the other side so it was not totally obvious I was going along with him and trying to make it easier.
I pulled back and fanned myself and said it had gotten a bit warm in here all of a sudden. I also commented on how good of a kisser he was. Fred was older but not in the least inexperienced. It had been a long time since I had been kissed like that and I could feel my body betraying me. I knew I was wet and I could feel my nipple were hard and straining. I had not really been this excited in a while.
Fred continued his quest to get me excited in the back of the limo and he was now nuzzling my neck and working the top of my dress down so my breast were fully exposed. I looked down and watch Fred manipulate my dress so he would have unrestricted access to my breast and now he was maneuvering the slit of the dress so my most private spot would be in easy access. I knew if I did not lift up off the seat it would be over for him and I got up and leaned over to get a drink out of the refrigerator. I told Fred I was overheating. As I was off the seat reaching for the water I could feel Fred Slide my dress up around my waist and I could hear him gasp as he saw I was not wearing any panties.
I asked Fred if he liked what he saw and he made a noise and moved in front of me and spread my legs so he could get between them. Fred was now licking my clit and began fingering my wet pussy as he tried desperately to devour my clit and all my juices flowing from my pussy.
Fred really knew how to get a woman ready for a good orgasm. Fred would bring me to the edge of cumming where I was desperate to cum and then he would stop and ask me to move or to change positions. I think by the time we were back to his penthouse I was ready to cum at least four times and was ready to get inside and have a good time with Fred.
Fred asked if I had something more comfortable to wear while he made drinks. I really did not need a drink but I went to the bathroom and changed into the nightie in my purse. Fred commented that I looked a lot more comfortable and a lot more delectable. I went over to the table where he had the drink and picked it up and took a sip. I asked what was in it and he said 100% pure Florida orange juice. Fred said he did not consume alcoholic beverages when he was entertaining a beautiful and sexy woman. Fred had all the lines.
Fred asked me to sit on the table and I did. I was sitting there sipping my orange juice and Fred put his glass down and went over to a cupboard and got a box and removed a dildo still in the plastic. Fred cut open the package and washed it off in the bar sink and poured some Astro Glide all over it and began to work it in and out of my pussy as he licked my clit. This time he worked the dildo harder and faster until I came and kept going until I thought I was going to die and I finally had to ask him to stop.
Fred again went over to the cabinet and came back with another new dildo still in the plastic and washed it and lubed it all up. This time he gave it to me and said I want to watch you make yourself cum. I worked it up and down my slit that was already wet with my juices and the Astro Glide from the other dildo. I teased myself with it rubbing it up and down my slit and then began working it in a little and then all the way out and back in some more and finally after a while I was bringing it all the way out and then ramming it all the way home until I finally came again.
Fred came over and took the dildo and then asked if I needed to rest some or if I was ready to go again. I said I could use some rest or go again and if I went again it would not take a lot to make me cum again. I was waiting for something to happen when Fred came over and dropped his robe and began to slip his hard cock into me. Fred was not big, just average and he knew what to do to give pleasure to the person he was with. I was on the verge of cumming twice before he was ready to cum and I could tell he was ready and began working the muscled in my pussy as I began rocking my hip to meet his thrust and after a minute I could feel Fred dumping his hot load into my pussy.
Fred stayed inside me for the longest time before he withdrew and then asked if I would shower with him. Fred said normally he did not shower with a woman he entertained, but said I was very special. We took a long hot shower together and after we just went to sleep. I awoke at about nine o’clock the next morning and went to the bathroom and came back to bed. I asked Fred if he would like to celebrate the sun rise and he smiled and thanked me and said no that he had not taken his medicine and would not be able to perform.
I leaned over and kissed Fred and thanked him for a wonderful night. I said I really meant that. Fred asked if I was going to be available for a date at another time and I said I would let him know. Fred said he had something special for me and handed me an envelope with cash in it. I looked at Fred and said I could not take it. Fred said it was a tip and I told him I had not place safe to keep it and I was due to be with another client at 11:00 A.M.
I met Bill at the marina and we went to the Fisherman’s Warf in the marina for lunch. Most of the people there were much like the ones I met at the Victorian Manor. I recognized one of the other gentlemen who was with Carol and he came over and told Bill it looked like he had a prize catch already. Bill beamed with delight as he smiled and said yes. The other gentleman – Karl said he was stag at the moment. I asked about Carol and he said she was a lot of fun, but she had another appointment for the day. Karl said he would book her for the week-end the next time. Bill said like wise here. There is nothing like having a date that you loose after you find one that is acceptable.
Karl mentioned that things were looking up as Buddy added more mature women to his escort service. Bill said yes, especially since the quality is so good. Then the two of them talked about how nice it was to have someone who was not a kid with them. Bill said I always feel like I am a baby sitter for some of the kids Buddy has and on top of that they do not know how to act in public. I made a mental not to get in contact with Carol and find out how she made out and if she was going to keep working for Buddy.
Bill and I had lunch and Karl joined us. I was made to feel like the prize at a fair since both of them were catering to me and trying to make me feel special and take their offer for the next week-end. I explained that I had other commitments and would have to get back with them. I thought this is getting more complicated – what would I tell my husband and family – sorry I have a date this week-end fucking a rich guy…
Bill asked me if I would mind if Karl spent the afternoon with us. I knew that meant that I would probable be expected to service both of them. I was thinking about it when Roberto came over and asked to join us. Bill looked at Karl and then to me and said it is up to the lady. I did not know what to say, did this mean I was going to service all three or was he just joining us for lunch. I was scared about the possibility of having to service three men all afternoon, when all of a sudden I said why not the more the merrier.
Karl and Bill exchanged looks and then looked at me and smiled and said I knew this was the prize catch and Karl agreed. We all ate lunch and there was a lot of chit chat about business and some other social events that were coming up in the near future and if they were going to be there. Roberto said he would like to go, but was having a lot of trouble finding a suitable date. Roberto complained all he could find were kids, who looked and acted like kids and ooed and awed at everything and were a down right embarrassment.
Karl mentioned that Buddy had a few new girls pointing at me and mentioning about Carol the night before. Karl mentioned that Carol was fantastic too. It must have been a hidden meaning that she was good in bed as the other two said they would have to give that a try. I looked at them and thought to myself and wondered if they would think I was good in bed. I had never heard other men talk about me and my husband never talked about what we did in out bedroom.
We had just finished eating lunch when Bill said he was going to spend the afternoon out in the bay and had to go as he had to have his date back by 5:00 P.M. and was wasting a lot of valuable time. Karl and Roberto got up and Roberto told the waiter to put it on his tab and a healthy tip too. We all walked out and down to the pier and there was a launch waiting to take us out a distance to a luxurious yacht.
Bill explained to me that there were three crew men and the captain on the yacht, but not to worry they would not be a bother and would be out of sight. Bill mentioned putting on a bikini and going up to the sundeck. I looked and said sure. I had a bikini that was new and purchased just for this occasion by Buddy.
The bikini was a hot pink micro string bikini. When I put it on I realized I was going to have to shave quite a bit so it would not be sticking out. I went into the shower and conveniently found everything I needed. As I was shaving I thought why am I bother to try to trim to fit and just shaved it all off. I thought it would grow back anyway. I finished shaving and rinsed off in the shower and went out on the deck. I saw myself in a full length mirror and wondered if they would like what they saw as there was not really much that could not be seen.
I got my answer as all three of them commented I looked good enough to eat. I thanked them and went over and accepted the drink I was offered. Bill called on the intercom to the captain and said he wanted to cruise and to stay away from other vessels. We headed toward open water and after about fifteen minutes and two drinks we were in open water and there were not any other boats within close sight.
Bill came over to me and asked if I would not be more comfortable topless? I looked at him and the other two and asked if I was topless was I going to be alone as they all had shirts on. Bill and Roberto answered quickly without words and had stripped off their shirts and Karl said yes and followed suite. Karl mentioned that I may get sunburned and offered to put some suntan oil on me. I looked at the others and said we could all oil each other. I got the oil and went over to Bill and poured the oil all over his back and worked it in and all around and then did his chest. I did the same with the other two.
Bill then took the oil and poured a lot on my shoulders and told Karl and Roberto to take turns on my back for now and he would do the rest. Roberto took the oil and got on his knees and worked on my legs. Roberto seemed to have a very light touch and had made his way up to the bikini bottoms and mentioned they were getting in the way. I said I could not imagine they were in the way and asked what we should do about it. I felt the strings on each side being pulled almost immediately by Karl and Roberto.
I was standing there nude in front of three obviously horny men who were all fondling my body. I could no distinguish who was doing what any more and Karl had stripped off his shorts and I saw out of the corner of my eye that Roberto was now taking off his shorts too. Bill was the last and he asked me to get up on a table and lay on it. Bill said he wanted to know what I tasted like before we went any further.
Bill, Karl and Roberto all took turns eating my pussy and sucking on my breast as I lay on the table. I was starting to shake from all the stimulation and having all of my vital parts stimulated at once. I said it was not fair that I could not do anything and Bill lowered the table some how and the next thing I knew was there was a hard cock pressing against my lips.
I had not really given a blow job in quite a few years as my husband John was normally a wham bang thank you m’am kind of a guy and as long as he got his rocks off that was all he was interested in and he did not really ask for getting a blow job. I did my best as it was hard to concentrate and I could tell that whoever it was he was doing all the work as I felt his cock sliding in and out of my mouth.
I could now feel a cock slipping into my pussy as the one in my mouth quickened the pace and without warning he began cumming like a fire hydrant. I missed the sensation of his cock thickening just before he came and was caught off guard and choked and gagged a bit before I got it under control. After I finished swallowing all his cum and licking him clean I casually asked do you always cum in gallons. It must have been a big boost to his ego as he said with a lot of enthusiasm only when I have such a hot number with me.
Roberto took Karl’s place at my mouth and I was now in more control and concentrated on giving him a good blow job. I licked his cock up and down and played with his balls as I began sucking more and more into my mouth and in a minute he was done. I think he came very fast as I had hardly had anything to do and he boasted that was the best blow job he had ever had and Karl agreed the same. At that time Bill was ready to cum and pulled his cock out and shot his load all over my belly.
I could tell the three guys were going to be out of action for a while and asked if the minded if I took a swim. I needed to get some of the oil off my body and some of the stickiness. We all went below and jumped in the water. It was not until after we were in the water for a while that I realized the pool was right in front of the bridge and the captain and crew were watching us all swim and play nude in the water.
I mentioned this to Bill and he said it was a bonus for the crew. I was still excited and hoped it would not be long before one of the guys were ready to go again and I started to get a bit frisky with them trying to encourage them for more. I looked up at the crew and thought they would be fun, but I did not want to ruin it for the guy who was paying me. I said it was about three thirty and it would take about a half an hour to get back to the dock and that would leave us with an hour to play before we got there.
Karl said he would be able to play a little but he did not think he would last very long and Roberto said the same that they both would like to try my pussy. I said let’s go and we went in to the stateroom. I started to give Roberto a blowjob and when he was hard he started to go slow as he slipped it in and out but he ended up like a rabbit and was soon pulling out and squirting on my belly. I wondered what it was with pulling out I was looking to feeling the hot cum squirting in me as I came at the same time. I think it must be a macho thing to pull out and squirt so everyone can see how much you can cum.
I gave Karl a bit of a blowjob and got him hard and he was done even faster than Roberto and finally Bill. Bill seemed like he was going to last longer as he stopped twice but he was done too. I was still very horny because each time I was ready to cum they would pull out and squirt all over my belly. I asked if anyone was ready for more and they all looked like they had all they could take.
Karl looked at Bill and said I’ll bet as hot as she is she could take on the crew also. Roberto said he thought so too and would love the show. Bill smiled and said why not – what do you think of me? I said it is your party. Bill called the captain on the intercom to come to the stateroom with two of the crew.
The captain and the two crewmen wasted no time in getting undressed. The captain was the first to eat my pussy and the two crewmen sucked on my nipples and after a few minutes and then trading places after each of them got to eat my pussy I began getting one hard cock after another pounding in my pussy. I had just finished one when he got dressed and left and the other crew man came into the cabin. He was a young man and look like a child.
Tom was the youngest of them and by the time he came in the other crewmen were getting dressed and so were my three hosts. Bill said if you do not mind I am going to shower and change before we get to shore and Karl and Roberto excused themselves too. I was left with Tom and he finally dropped his shorts and revealed a nice fat cock. His cock was not very long just about six inches but it must have been as thick as a summer sausage. I was a bit worried it would hurt, but after all I had been thru I was amazed at how easily I accommodated him.
Tom took his time and after a while be began to increase the tempo and I could feel his cock swell as he was ready to cum and I whispered in his ear to cum inside me. Tom pushed harder and stretched my pussy more than it had ever been stretched and finally dumped his load deep in my pussy. Tom stayed inside me for a while and then said he had to go and got dressed and left. I took a quick shower and dressed and as I came out of the stateroom I could see the dock coming into view. I could see the limo waiting there on the dock waiting it was 5:00 P.M.
I rode the limo back to Buddy’s office and he said the men had all requested I get a bonus and he handed me $500.00. I took the money and wondered how much he skimmed off the top and he said the limo would take me back to my brothers and gave me his card. He mentioned that I could earn two thousand dollars to spend the next weekend with Fred. I said I would have to think about it.
I rode the limo back to my brothers and the limo driver handed me three envelopes and said he was instructed not to give them to me until after I met with Buddy, so he was sure I was the only one who knew what was in the envelopes. Each of the envelopes had two thousand dollars and one from Bill had a note that he would like my company again and he would make sure he had more cash for a tip the next time. I had made six thousand five hundred dollars, worked off my brother’s debt, and had about a thousand dollars worth of clothes. I sat there thinking as I went into his house to find him sitting there naked on the couch with a smile on his face.
Bo said he was glad to see me and had a thousand dollars in cash on the table and said Buddy said that was bonus money because I brought him such good luck and that my total debts are paid in full.
I looked at Bo and asked why he was sitting there naked and he just smiled and said he really enjoyed what I did for him and he only wanted to repay the favor and said he could not get over me giving him a blowjob and was going nuts thinking about getting another one and eating my pussy.
I looked at Bo and said why not and got undressed and we did a sixty nine there on the floor until both of us came and then after a brief rest I sucked him again until he was hard again and he mounted me from behind and pounded away for a good ten minutes until he came again.
I got cleaned up and ready to go back him and Bo kissed me and asked when I was coming to visit again. I thought about Buddy and all the money I made and said it may be sooner than you think.
I arrived on Friday evening and the door was open so I went in. I was shocked to see my brother tied to the kitchen chair with his hands behind his back and feet tied to the legs of the chair and a man repeatedly punching him in the face. My brother looked terrible. His face was all swollen and blood was coming out of the many cuts all over his face and nose. I thought he was going to die and I started screaming at him to stop it and I yelled I was calling the cops.
The man was across the room faster than I could react and before I realized it he had taken my cell phone and had me in some kind of hold with my arm behind my back and I had to keep standing on my top toes to keep the pain down. The man looked at my brother and then at me and said maybe your pretty girlfriend would be willing to work off your debt this weekend and if she does I will not break both your arms and legs. My brother looked terrified as the man spoke and then looked at me with the same terrified look on his face.
The man asked me my name and I said Eve. He said well Eve you have a very nice face and I think under that baggy sweat shirt you may even have a nice body to go with it. He said he was going to give me a choice. He said I could stay and watch him break both arms and legs of my brother and he would be satisfied for a while that that was an interest payment on the money Bo owed the loan shark, or I could work it off for him and his debt would be paid if I cooperated and was any good at satisfying his customers.
I said what kind of customers and he said mostly married men who do not get enough at home and are looking for some fun. I realized he was talking about sex and using me as a prostitute to get the money my brother owed him. My brother had since passed out from the beating he already received and was not saying anything. I asked how long and what type of guarantee I would have that he would not renege on our deal. I said I had only briefly known him – my brother, but I might be willing to help him out if I had some guarantees.
We had arranged a deal that I would work for him the rest of the weekend until Sunday at 5:00 P.M. and the debt would be clear and I was free to go and there would be no attempts to try to blackmail me or anything else. I was scared to death of what I was agreeing to and at the same time there was a certain excitement about having to have sex with strange men. I have been faithful to my husband for the past twenty years and had not really thought about cheating on him.
The loan shark said before he had the final agreement he needed to see how good I looked and if I could perform sexually. I was a bit squeamish at first and then I thought what the heck if I was going to do it with other complete strangers why worry about this guy now. He told me to undress and when I did he said I should not hide such a sexy body like that under all the baggy clothes I wore. I smiled and asked what he wanted me to do. He said for starters I want you to see if you can suck cock good enough. I said I thought that would be coming and he said yes. Then he surprised me and told me to suck Bo’s cock and make him cum even though he was passed out. He said if I could bet him to cum in a short amount of time he would know for certain that I would be good enough.
I was not really sure I could give my brother a blow job and make him cum. There were so many things running thru my head at the time. I did not really care to give a blow job and now I was going to give one to my brother – that was incest. I was thinking about it when the loan shark told me he was finished untying him and to get the show on the road. I went over and fumbled with his belt and after a few seconds I got it open and started working on unzipping his pants. I was trying to work on him when I looked up and there was the loan shark with a knife and then he cut the pants and underwear right off and said that ought to make it a little easier for you.
I spread his legs apart and took hold of his limp cock in one hand and began to stroke it a little and then I started to lick the head and suck it into my mouth. I was hoping Bo would not say anything to give me away or to make it more difficult. I got him hard faster than I expected and in a few seconds he was rocking his hips and grabbing at my head to go faster and to suck more into my mouth. I took it all the way into my mouth down to the base and sucked and licked him a little before I pulled back up and went down again and in another second he was cumming in my mouth. I opened my mouth to show the loan shark that he came and he said good job and put his cock in my mouth and said do me now too.
I took the load sharks cock into my mouth and licked the head and put my tongue into the tip of his cock and then sucked him all they way down and back up and did the same thing all over again. I played with his nuts stroking then and tickling his anus with my finger as I sucked him all the way back into my mouth. I thought of their sizes that neither of them was very long or fat. I thought of Bud and how he was and then compared and made a mental note the next time to pay more attention to his size. I was a bit surprised when the loan shark came so fast. I had cum dripping down my chin and looked up at him and asked if he was satisfied.
I was thinking about what I had just done in the matter of ten minutes I cheated two times on my husband with two men, of which one was my brother. I thought I found myself enjoying myself after getting over the initial revulsion of having sex with someone else and that I was actually looking forward to more. I was feeling rather wet at the time and hoped in one way they would not notice and in another way I hoped they would and one of them would eat my pussy and give me some hard cock and make me cum.
Bo was looking thru his swollen eyes and I knew he would not be able to eat my pussy, but he would be lucky to be able to get it up again after having had such beating. Bo surprised me that he was standing there with his hard cock pointing at me and he went over to me and spread my legs and began to rub his cock up and down my slit and then put the tip on my clit and rubbed it all around and told me he had dreamed about this for a long time and now I was really going to get it and he plunged all the way into my pussy. Bo was ready to cum when all of a sudden the loan shark burst out DO NOT CUM INSIDE HER!
Bo pulled out and shot his load all over the front of me. The loan shark said he had a special customer for me and I would work off half of my brother’s debt in the first job. He explained he had a older gentleman who wanted a mature woman to go out on a date with that did not look like a kid and he was willing to pay extra for the date and he had just described me to the man and he agreed to pay $2,000.00 for the night if I looked as good as I was described and maybe even a bonus.
Bo looked at the loan shark and said that was what he owed him. The loan shark explained cost and interest charges to him and if he in the mood for another beating he could arrange it. The loan shark also explained he had a deal with your girlfriend to work off your debt by working for me all weekend until 5:00 P.M. on Sunday. I agreed and said I had made the agreement but I did not realize I would make as much in one night as what was owed. The loan shark agreed that a deal was a deal and if I wanted to back out he could still break Bo’s arms and legs.
The loan shark said the first thing we need to do is to go shopping. You can not go out on a date in sweats and you will need to look very sexy. He said Frederick’s of Hollywood should due nicely and we left.
I was amazed that women would actually wear some of the clothes they sold there in public. I was looking a long evening gown that had a slit up one side to the top of the leg and a deep plunge down the middle and an open back. I looked at him and said you might as well almost go nude. He looked at me and with all seriousness said that is the whole idea. He told the girl he wanted one like I was looking at in my size to go.
I tried on a couple of them and the sales girl said she would have to have one altered for me as the two they had that had the right size one was too tight and would be very uncomfortable and the other was a bit looser on the top and would more than likely fall off if I was not careful. He said we would take the one that was too large and we would not wait. The sales woman said she could put a couple of darts in near the top so it would fit better. He was a bit impatient and said only if it does not take too long.
I figured she needed a little help and I asked where the lingerie was. The loan shark said that is a good idea and followed me and another sales woman to where they had all kinds of lingerie. He asked if I could try some on and she looked at me and then back to him and said timidly sure if she does not mind. He replied she does not mind. He picked out two and said try them on and let me see what you look like.
I went into the changing room and the one woman said he is quite demanding. I said I know and I will be glad when the week-end is over. She asked why and she was the only one who noticed I had a wedding ring on. I said I agreed to try anything until Sunday night in order to avoid a lot of pain and suffering. She said I was a saint and she would just let the asshole crash and burn.
I put on the first nightie a long sheer thing with spaghetti straps and a deep plunge. There was not much to it and if you move the straps it would fall to the floor. I thought of my husband and wondered why we even bothered it would only be on for a minute before they would have it off. I looked in the mirror and thought I would be walking out into he store practically nude and all the people would see me and would be able to see thru the thin material. I got a little excited at the thought of it.
I walked out from the dressing room and he was standing there talking to another man who was a bit older and his wife was looking at a nightie. His wife was a lot younger and he commented on how sexy I looked and called his wife to see also. I paraded around so they could all see and then went in and got on the other one, which was a short thing with a g-string. I did the same and he said he would take both and the other man and his wife were there looking like they were stunned.
The other man asked his wife to try one on and let him see how she looked in it and at the loan shark and said wait until you see her. I looked at her and she had the fear of God look on her face and I said it is not that bad – just do not look anyone in the face except your husband and you will be okay. Just think you are in the bedroom. It was actually very exciting for me knowing all the people could see me and the men would be excited by what they were seeing.
The loan shark said we would wait to see her as it would be rude to leave his new friend without someone to comment on the outfit too. I stood there watching too. She came out in the same long nightie I wore and she looked scared. I told her she looked great and to smile and she seemed to relax and smiled. The man said you look sexy enough to eat right here and any man would be proud to have you with him. It must have been what she needed because she looked for approval from the loan shark and asked what he thought.
The loan shark said he could get people who would be willing to pay to see her like that and they would love to share her in bed. The man smiled and said I told you that you looked great and you could be a great hooker if you wanted. She laughed and said what man would pay to have sex with me when there were hundreds and thousands of teenage hookers and other in their twenties who were younger and firmer than she was.
The loan shark looked at her husband and then who me and then to her and said I know hundreds of guys who want a date with a mature woman who would fulfill their fantasies. These men are older and more refined and are not looking for young they are looking for women like you and her pointing to me who are classy and respectable and would be acceptable in public. Then he added that the money is good also. You could earn $500.00 for the evening, plus tips if you were nice and gave her a wink and a smile and looked back at her husband. He pulled out a card that had his name on it and a modeling and escort service name on it and handed it to her husband. I would be available to help her pick out her outfits so she would look sexy and alluring, but not slutty. Then he pointed to me and said isn’t that right Eve. I replied yes.
She looked at me and asked if I was not married to him and I replied a little more emphatically No than necessary. I said I had a situation and needed a lot of money and could not wait and in the course of the weekend I would make that much money and my debts would be cleared. She looked at her husband and then back to the loan shark who for the first time said call me Buddy. She said how much money. Buddy looked at her and said I could get you $400.00 a night. The man said is that all night or just the evening.
Buddy explained that typically a job would start at 8:00 P.M. and would end at 1:00 A.M. and that it would last longer if the woman wanted it to last longer and then there would be bonus money involved and that would be negotiated directly between you and the person you are escorting. There are others who like starting at 9:00 P.M. or 10:00 P.M. and stay out until 2:00 A.M. to 3:00 A.M. Buddy said he only provided to service opportunity and they rest was up to them.
I was listening intently to the offer and what he was saying as I knew what was expected in the end. The woman’s husband Ralph asked how many weekends Carol would have to work if she wanted to work. Buddy said it was entirely voluntary and it was not always weekends and some times it could involve travel as he had a customer who wanted a date to go on a cruise to Alaska with him and he had a woman take him up on it.
Carol said if you were picking out an outfit for me what would you pick out. Buddy looked her over and we all went over to where the dresses where and got one that accentuated her waist line since her breast were not as large as mine and she had a nicer bottom. Carol had him pick out a second outfit and said just to see how you would have new dress.
Buddy picked out a long skirt and an adjustable wrap blouse that could be adjusted so she could choose how much cleavage she was going to show. Buddy commented some men are more interested in how sexy and alluring you look and some are more interested in how much of you they can see. This is an outfit you can do both. Ralph asked Carol to try it on and get our approval. I had the distinct feeling Ralph was going to ask Buddy when she could start working.
Carol went in and before she was all the way in the dressing room Ralph had asked all the particulars and if sex was required. Buddy said sex was not required but would be a plus if she was going to get a bonus and if she was going to have some regular clients who asked for her specifically. Buddy mentioned several women he had who were always busy with the same clients every time they came to town. Ralph asked if they were all from out of town or if there were any locals. Buddy said I call and tell you what I have and show you the pictures of the client and give you their likes and dislikes… Then you decide. Most escort services are $300.00 - $400.00 per night and some higher. Suppose a man who is not as appealing to be with in public wants a date and the girl decides she would go out with him if she got more money she could get more, but it would have to be agreeable to all parties involved. I have a girl Katie who will go out with fat men for $750.00 a night and a lot of the other girls will not do it at all. So Katie is always in high demand.
Carol came out and modeled the outfit for us and Ralph said you could be an escort looking like that. Buddy said I could get you a date tonight at one of the nicest restaurants in town. Carol looked at Ralph and then to Buddy and then to me and then said it would have to be later as they did not have the money to purchase all the clothes now. Buddy said I will take care of it as a gift if you are going to do this for me. They all agreed and Buddy said a limo would pick her up at 9:00 P.M. and have her back by 3:00 A.M. if it was acceptable to both. The all agreed.
Ralph asked when she would get paid for going out and Buddy said they are all paid in cash after each date. Carol asked about the bonuses and Buddy said they are paid to you directly by the client. What you do to get it and what you do with the money is your business. Buddy looked at me and said come on Eve you have work to do and that I was his new good luck charm.
I had taken all the things in that had just transpired in the past few hours and for some reason I was actually thinking about becoming an escort. I hated the job I was working at and we needed the extra money and since I would be paid in cash I would not have to report on taxes any of it. I was thinking about all the possibilities as we drive to Buddy’s office.
The office was in an upscale office complex and there was a lot of security and it appeared very professional. On the way into the elevator one very distinguished older man was getting out as we were getting in and he said hello to Buddy and then winked at me and asked Buddy if I was a new girl? Buddy replied a very selective one. The man answered looking at me that he would be willing to pay extra for a date with me. Buddy replied that Sunday was open until 5:00 P.M. and after that I was done for this week. He looked at me and then said double the normal rate and they agreed and he said have her ready for lunch at 11:00 A.M. at the marina and they would spend the afternoon on the yacht.
I looked at Buddy and did not say anything and then to the man and smiled and in the sexiest voice I said see you later.
We arrived in Buddies office and he told me to change into the evening gown as the other man who was interested in going out with me also worked in this building and he would be picking me up here. Buddy had gotten me a nice handbag to go with my gown a little large than normal so it would fit the nightie he got me. I was to take it with me as we would be coming back to the penthouse when we finished dinner and I would be needing to relax and have cocktails after we got back and since I was paying off my brothers debt I would be required to provide sexual services at not additional charge to the client.
I got dressed and waited very anxiously for him to arrive. Fred arrived promptly at 7:30 P.M. and was very mature looking. I thought he looked old enough to be my father. Fred commented on how sexy I looked and that he was glad I did not look like his granddaughter. Fred explained he hated going out to dinner with someone who looked like a child and not a date and how hard it was to get a sexy mature woman to have dinner with. He went on for a minute or two and then we left, after Buddy told him I had to be back first thing in the morning as I had another customer for lunch.
Fred looked at Buddy and asked if it was Bill? Buddy replied yes and smiled. Fred said he was always doing that and they would have to talk about Bill getting the same girls. Buddy said it was just business and Bill had met me in the elevator and what could I say when he said he was willing to pay double the going rate. Fred smiled and looked to me and said let’s go.
We went to the Victorian Manor for dinner and cocktails and Fred was positively beaming as a lot of older gentlemen and their wives were arriving for dinner and going thru the niceties. One of the men whispered something to him and he blushed and smiled and said maybe another time. One of the ladies said it was nice to see him getting out in public again since the loss of his wife and it was nice that he finally had someone more appropriate for a date than the little children he brought to dinner before. I looked at Fred and smiled and said it looks like I am a hit with some of your friends.
Fred ate very slowly for a man and half way thru dinner he asked if I could adjust my dress so he could see a little more cleavage. I smiled and adjusted the straps and asked how that was and he smiled ands said he was hoping for a bit more and mentioned to a woman a little older who was almost falling out of her top. I asked if I should just go topless. He said no, it would not be appropriate but a little more revealing would be nice and said it would influence his tip, but cautioned me on looking slutty.
I went to the ladies room and took off the gown in one of the stalls, which were very roomy for a restroom. I took the darts out of the sides of the dress so it would open more in the front and put it back on. I was looking in the mirror when I saw Carol coming in the restroom and asked how she was enjoying herself.
Carol smiled and said very nicely I just have to get rid of my panties as they are positively soaked. She quickly explained that shortly after they left Buddy called and said he had a date and gave Ralph $450.00 in cash as he picked me up and brought me here and introduced me to Bill. She explained Bill was a horny old goat and talked dirty to her when ever there was not anyone in ear shot. Carol said he offered her $100.00 each for her bra and panties and to come in and take them off and come out and give then to him at the table. Carol said Ralph would never know and besides he had to take Viagra to get it up and some times it did not work. Carol smiled and said I think if it goes right I am going to get lucky with Bill. I said make sure you do not do it for free. I could not believe what I had just said. We hugged and went our separate ways.
I apologized to Fred for taking so long, but I had to alter the dress to get the desired effect. Fred beamed and readily approved and said it was fantastic. Fred went on how sexy I was looking and how all the other men would be envious of him having such a hot date. I asked if all the men were not with their wives and Fred replied that most of them were widowers and only a few were married. Fred explained the two women who came over and introduced themselves to us were wives of the men they were with and the rest of the men were with dates.
I looked around and asked Fred if he had dated any of the other women there and he said yes, but none compared to me. I blushed and he said no really you will be a prize as you are more mature and have the look of being brought up properly, not like most of the young girls who are here now. I looked around and took a real good assessment of the women and had to agree most of them looked out of their element. I made several mental notes and then asked Fred if he like having a variety of women to go out with or just a few.
Fred said he had not found one until now that he would really consider going out with on a regular basis and this was sort of the proving grounds before going out to some of the other restaurants and events. Fred asked how I liked the theater and I said we are not talking about the movie theater I take it and he said no – Broadway. I replied I had never been there and he asked how I would like to go. I said it would be great, but not this week-end. Fred replied that he knew already and kind of got sad.
I told Fred I would have to make some special arrangements to go as it would require me to leave my regular job for a while. I told him I was not a regular girl working for Buddy even though he wanted me to be a regular. Fred said he could understand why at the price he charged for me. Fred said it is normally $750.00 per night for the girls and the young ones were expected to have sex with us. He said that sex was up to me and I would have to tip extra for it. I smiled and said I was glad to have that information. Fred looked like he let the cat out of the bag and got caught and then smiled and said only willing to help someone who I am hoping to see more of in the future.
I sat there thru the rest of dinner quietly eating and making sure I leaned over enough for Fred to get a good view and to look more proper when people came over and greeted us. By the time dinner was over Fred was the envy of most of the men in the place and a lot of the women also commented on how radiant I looked with Fred.
Fred paid the bill and we left. I was holding his arm and we were getting into the limo when another couple came over and commented on how nice we looked together and Fred smiled even more. The woman commented to me that I must be special as she had not seen Fred smile and look so happy in a long time. Then she said to Fred that he would have to bring me out to the house for dinner some time. Fred smiled and said we will see.
I looked up at the driver and Fred noticed and pressed a button and a dark glass came up and we could no long see the driver. Fred pressed another button and talked to the driver and told him to take the long way back to the penthouse and he was turning off the intercom.
Fred asked if I minded and leaned over and kissed me. A soft gentle kiss like that of a lover not someone trying to get laid by a hooker. Fred took his time kissing me and gently rubbing my back and shoulders. I could tell he was trying to get more of a view down my dress without being over obvious about it. I decided to help him and dropped my shoulder so the strap would fall easier as he rubbed my shoulder and back and I turned and did the same on the other side so it was not totally obvious I was going along with him and trying to make it easier.
I pulled back and fanned myself and said it had gotten a bit warm in here all of a sudden. I also commented on how good of a kisser he was. Fred was older but not in the least inexperienced. It had been a long time since I had been kissed like that and I could feel my body betraying me. I knew I was wet and I could feel my nipple were hard and straining. I had not really been this excited in a while.
Fred continued his quest to get me excited in the back of the limo and he was now nuzzling my neck and working the top of my dress down so my breast were fully exposed. I looked down and watch Fred manipulate my dress so he would have unrestricted access to my breast and now he was maneuvering the slit of the dress so my most private spot would be in easy access. I knew if I did not lift up off the seat it would be over for him and I got up and leaned over to get a drink out of the refrigerator. I told Fred I was overheating. As I was off the seat reaching for the water I could feel Fred Slide my dress up around my waist and I could hear him gasp as he saw I was not wearing any panties.
I asked Fred if he liked what he saw and he made a noise and moved in front of me and spread my legs so he could get between them. Fred was now licking my clit and began fingering my wet pussy as he tried desperately to devour my clit and all my juices flowing from my pussy.
Fred really knew how to get a woman ready for a good orgasm. Fred would bring me to the edge of cumming where I was desperate to cum and then he would stop and ask me to move or to change positions. I think by the time we were back to his penthouse I was ready to cum at least four times and was ready to get inside and have a good time with Fred.
Fred asked if I had something more comfortable to wear while he made drinks. I really did not need a drink but I went to the bathroom and changed into the nightie in my purse. Fred commented that I looked a lot more comfortable and a lot more delectable. I went over to the table where he had the drink and picked it up and took a sip. I asked what was in it and he said 100% pure Florida orange juice. Fred said he did not consume alcoholic beverages when he was entertaining a beautiful and sexy woman. Fred had all the lines.
Fred asked me to sit on the table and I did. I was sitting there sipping my orange juice and Fred put his glass down and went over to a cupboard and got a box and removed a dildo still in the plastic. Fred cut open the package and washed it off in the bar sink and poured some Astro Glide all over it and began to work it in and out of my pussy as he licked my clit. This time he worked the dildo harder and faster until I came and kept going until I thought I was going to die and I finally had to ask him to stop.
Fred again went over to the cabinet and came back with another new dildo still in the plastic and washed it and lubed it all up. This time he gave it to me and said I want to watch you make yourself cum. I worked it up and down my slit that was already wet with my juices and the Astro Glide from the other dildo. I teased myself with it rubbing it up and down my slit and then began working it in a little and then all the way out and back in some more and finally after a while I was bringing it all the way out and then ramming it all the way home until I finally came again.
Fred came over and took the dildo and then asked if I needed to rest some or if I was ready to go again. I said I could use some rest or go again and if I went again it would not take a lot to make me cum again. I was waiting for something to happen when Fred came over and dropped his robe and began to slip his hard cock into me. Fred was not big, just average and he knew what to do to give pleasure to the person he was with. I was on the verge of cumming twice before he was ready to cum and I could tell he was ready and began working the muscled in my pussy as I began rocking my hip to meet his thrust and after a minute I could feel Fred dumping his hot load into my pussy.
Fred stayed inside me for the longest time before he withdrew and then asked if I would shower with him. Fred said normally he did not shower with a woman he entertained, but said I was very special. We took a long hot shower together and after we just went to sleep. I awoke at about nine o’clock the next morning and went to the bathroom and came back to bed. I asked Fred if he would like to celebrate the sun rise and he smiled and thanked me and said no that he had not taken his medicine and would not be able to perform.
I leaned over and kissed Fred and thanked him for a wonderful night. I said I really meant that. Fred asked if I was going to be available for a date at another time and I said I would let him know. Fred said he had something special for me and handed me an envelope with cash in it. I looked at Fred and said I could not take it. Fred said it was a tip and I told him I had not place safe to keep it and I was due to be with another client at 11:00 A.M.
I met Bill at the marina and we went to the Fisherman’s Warf in the marina for lunch. Most of the people there were much like the ones I met at the Victorian Manor. I recognized one of the other gentlemen who was with Carol and he came over and told Bill it looked like he had a prize catch already. Bill beamed with delight as he smiled and said yes. The other gentleman – Karl said he was stag at the moment. I asked about Carol and he said she was a lot of fun, but she had another appointment for the day. Karl said he would book her for the week-end the next time. Bill said like wise here. There is nothing like having a date that you loose after you find one that is acceptable.
Karl mentioned that things were looking up as Buddy added more mature women to his escort service. Bill said yes, especially since the quality is so good. Then the two of them talked about how nice it was to have someone who was not a kid with them. Bill said I always feel like I am a baby sitter for some of the kids Buddy has and on top of that they do not know how to act in public. I made a mental not to get in contact with Carol and find out how she made out and if she was going to keep working for Buddy.
Bill and I had lunch and Karl joined us. I was made to feel like the prize at a fair since both of them were catering to me and trying to make me feel special and take their offer for the next week-end. I explained that I had other commitments and would have to get back with them. I thought this is getting more complicated – what would I tell my husband and family – sorry I have a date this week-end fucking a rich guy…
Bill asked me if I would mind if Karl spent the afternoon with us. I knew that meant that I would probable be expected to service both of them. I was thinking about it when Roberto came over and asked to join us. Bill looked at Karl and then to me and said it is up to the lady. I did not know what to say, did this mean I was going to service all three or was he just joining us for lunch. I was scared about the possibility of having to service three men all afternoon, when all of a sudden I said why not the more the merrier.
Karl and Bill exchanged looks and then looked at me and smiled and said I knew this was the prize catch and Karl agreed. We all ate lunch and there was a lot of chit chat about business and some other social events that were coming up in the near future and if they were going to be there. Roberto said he would like to go, but was having a lot of trouble finding a suitable date. Roberto complained all he could find were kids, who looked and acted like kids and ooed and awed at everything and were a down right embarrassment.
Karl mentioned that Buddy had a few new girls pointing at me and mentioning about Carol the night before. Karl mentioned that Carol was fantastic too. It must have been a hidden meaning that she was good in bed as the other two said they would have to give that a try. I looked at them and thought to myself and wondered if they would think I was good in bed. I had never heard other men talk about me and my husband never talked about what we did in out bedroom.
We had just finished eating lunch when Bill said he was going to spend the afternoon out in the bay and had to go as he had to have his date back by 5:00 P.M. and was wasting a lot of valuable time. Karl and Roberto got up and Roberto told the waiter to put it on his tab and a healthy tip too. We all walked out and down to the pier and there was a launch waiting to take us out a distance to a luxurious yacht.
Bill explained to me that there were three crew men and the captain on the yacht, but not to worry they would not be a bother and would be out of sight. Bill mentioned putting on a bikini and going up to the sundeck. I looked and said sure. I had a bikini that was new and purchased just for this occasion by Buddy.
The bikini was a hot pink micro string bikini. When I put it on I realized I was going to have to shave quite a bit so it would not be sticking out. I went into the shower and conveniently found everything I needed. As I was shaving I thought why am I bother to try to trim to fit and just shaved it all off. I thought it would grow back anyway. I finished shaving and rinsed off in the shower and went out on the deck. I saw myself in a full length mirror and wondered if they would like what they saw as there was not really much that could not be seen.
I got my answer as all three of them commented I looked good enough to eat. I thanked them and went over and accepted the drink I was offered. Bill called on the intercom to the captain and said he wanted to cruise and to stay away from other vessels. We headed toward open water and after about fifteen minutes and two drinks we were in open water and there were not any other boats within close sight.
Bill came over to me and asked if I would not be more comfortable topless? I looked at him and the other two and asked if I was topless was I going to be alone as they all had shirts on. Bill and Roberto answered quickly without words and had stripped off their shirts and Karl said yes and followed suite. Karl mentioned that I may get sunburned and offered to put some suntan oil on me. I looked at the others and said we could all oil each other. I got the oil and went over to Bill and poured the oil all over his back and worked it in and all around and then did his chest. I did the same with the other two.
Bill then took the oil and poured a lot on my shoulders and told Karl and Roberto to take turns on my back for now and he would do the rest. Roberto took the oil and got on his knees and worked on my legs. Roberto seemed to have a very light touch and had made his way up to the bikini bottoms and mentioned they were getting in the way. I said I could not imagine they were in the way and asked what we should do about it. I felt the strings on each side being pulled almost immediately by Karl and Roberto.
I was standing there nude in front of three obviously horny men who were all fondling my body. I could no distinguish who was doing what any more and Karl had stripped off his shorts and I saw out of the corner of my eye that Roberto was now taking off his shorts too. Bill was the last and he asked me to get up on a table and lay on it. Bill said he wanted to know what I tasted like before we went any further.
Bill, Karl and Roberto all took turns eating my pussy and sucking on my breast as I lay on the table. I was starting to shake from all the stimulation and having all of my vital parts stimulated at once. I said it was not fair that I could not do anything and Bill lowered the table some how and the next thing I knew was there was a hard cock pressing against my lips.
I had not really given a blow job in quite a few years as my husband John was normally a wham bang thank you m’am kind of a guy and as long as he got his rocks off that was all he was interested in and he did not really ask for getting a blow job. I did my best as it was hard to concentrate and I could tell that whoever it was he was doing all the work as I felt his cock sliding in and out of my mouth.
I could now feel a cock slipping into my pussy as the one in my mouth quickened the pace and without warning he began cumming like a fire hydrant. I missed the sensation of his cock thickening just before he came and was caught off guard and choked and gagged a bit before I got it under control. After I finished swallowing all his cum and licking him clean I casually asked do you always cum in gallons. It must have been a big boost to his ego as he said with a lot of enthusiasm only when I have such a hot number with me.
Roberto took Karl’s place at my mouth and I was now in more control and concentrated on giving him a good blow job. I licked his cock up and down and played with his balls as I began sucking more and more into my mouth and in a minute he was done. I think he came very fast as I had hardly had anything to do and he boasted that was the best blow job he had ever had and Karl agreed the same. At that time Bill was ready to cum and pulled his cock out and shot his load all over my belly.
I could tell the three guys were going to be out of action for a while and asked if the minded if I took a swim. I needed to get some of the oil off my body and some of the stickiness. We all went below and jumped in the water. It was not until after we were in the water for a while that I realized the pool was right in front of the bridge and the captain and crew were watching us all swim and play nude in the water.
I mentioned this to Bill and he said it was a bonus for the crew. I was still excited and hoped it would not be long before one of the guys were ready to go again and I started to get a bit frisky with them trying to encourage them for more. I looked up at the crew and thought they would be fun, but I did not want to ruin it for the guy who was paying me. I said it was about three thirty and it would take about a half an hour to get back to the dock and that would leave us with an hour to play before we got there.
Karl said he would be able to play a little but he did not think he would last very long and Roberto said the same that they both would like to try my pussy. I said let’s go and we went in to the stateroom. I started to give Roberto a blowjob and when he was hard he started to go slow as he slipped it in and out but he ended up like a rabbit and was soon pulling out and squirting on my belly. I wondered what it was with pulling out I was looking to feeling the hot cum squirting in me as I came at the same time. I think it must be a macho thing to pull out and squirt so everyone can see how much you can cum.
I gave Karl a bit of a blowjob and got him hard and he was done even faster than Roberto and finally Bill. Bill seemed like he was going to last longer as he stopped twice but he was done too. I was still very horny because each time I was ready to cum they would pull out and squirt all over my belly. I asked if anyone was ready for more and they all looked like they had all they could take.
Karl looked at Bill and said I’ll bet as hot as she is she could take on the crew also. Roberto said he thought so too and would love the show. Bill smiled and said why not – what do you think of me? I said it is your party. Bill called the captain on the intercom to come to the stateroom with two of the crew.
The captain and the two crewmen wasted no time in getting undressed. The captain was the first to eat my pussy and the two crewmen sucked on my nipples and after a few minutes and then trading places after each of them got to eat my pussy I began getting one hard cock after another pounding in my pussy. I had just finished one when he got dressed and left and the other crew man came into the cabin. He was a young man and look like a child.
Tom was the youngest of them and by the time he came in the other crewmen were getting dressed and so were my three hosts. Bill said if you do not mind I am going to shower and change before we get to shore and Karl and Roberto excused themselves too. I was left with Tom and he finally dropped his shorts and revealed a nice fat cock. His cock was not very long just about six inches but it must have been as thick as a summer sausage. I was a bit worried it would hurt, but after all I had been thru I was amazed at how easily I accommodated him.
Tom took his time and after a while be began to increase the tempo and I could feel his cock swell as he was ready to cum and I whispered in his ear to cum inside me. Tom pushed harder and stretched my pussy more than it had ever been stretched and finally dumped his load deep in my pussy. Tom stayed inside me for a while and then said he had to go and got dressed and left. I took a quick shower and dressed and as I came out of the stateroom I could see the dock coming into view. I could see the limo waiting there on the dock waiting it was 5:00 P.M.
I rode the limo back to Buddy’s office and he said the men had all requested I get a bonus and he handed me $500.00. I took the money and wondered how much he skimmed off the top and he said the limo would take me back to my brothers and gave me his card. He mentioned that I could earn two thousand dollars to spend the next weekend with Fred. I said I would have to think about it.
I rode the limo back to my brothers and the limo driver handed me three envelopes and said he was instructed not to give them to me until after I met with Buddy, so he was sure I was the only one who knew what was in the envelopes. Each of the envelopes had two thousand dollars and one from Bill had a note that he would like my company again and he would make sure he had more cash for a tip the next time. I had made six thousand five hundred dollars, worked off my brother’s debt, and had about a thousand dollars worth of clothes. I sat there thinking as I went into his house to find him sitting there naked on the couch with a smile on his face.
Bo said he was glad to see me and had a thousand dollars in cash on the table and said Buddy said that was bonus money because I brought him such good luck and that my total debts are paid in full.
I looked at Bo and asked why he was sitting there naked and he just smiled and said he really enjoyed what I did for him and he only wanted to repay the favor and said he could not get over me giving him a blowjob and was going nuts thinking about getting another one and eating my pussy.
I looked at Bo and said why not and got undressed and we did a sixty nine there on the floor until both of us came and then after a brief rest I sucked him again until he was hard again and he mounted me from behind and pounded away for a good ten minutes until he came again.
I got cleaned up and ready to go back him and Bo kissed me and asked when I was coming to visit again. I thought about Buddy and all the money I made and said it may be sooner than you think.