A Thousand Bucks Ch. 03

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You may want to read the previous chapters before this one. This one could be put in so many different categories. Thanks to all who have commented. Also a big thank you to Estragon for making this story a much better read.


As I mentioned earlier, I offered a thousand dollars to boyfriends if they agreed to let me have sex with their girlfriends. I had sex with over thirty single women with their boyfriends’ approval. I also made the same offer to husbands of a thousand dollars to fuck their wives.

I couldn’t believe the takers that I received. Another thing was even though they took the money, most didn’t do it for that reason. They had fantasies and wanted to see their wife having sex with another man. The money was just an incentive to make them go for it. Many regretted it afterward.

I have one more couple to tell you about. Lillian and Fred, who have been married for forty years, were different. Lillian was now fifty-eight and Fred just turned sixty-two.

Fred recently underwent chemotherapy and is not in the best of health. He is not able to get an erection. He and Lillian are truly in love and would do anything for one another.

Fred saw my ad and sent me an e-mail. He said that Lillian has never been with another man. They got married when she was only eighteen. She had two miscarriages and wasn’t able to conceive. They took in foster kids up till about five years ago. They felt they were now too old for the rigors of foster parenting.

Fred said he had spoken with Lillian and at first she didn’t want any part of having sex with another man. Fred pleaded with her and said that he wanted her to be happy and she should try it at least once in her life. He mentioned that he had often thought about her with another man throughout the years.

I knew I was becoming softer on the couples I have been with. I no longer hated everyone. I was going to make Lillian and Fred my last couple. After talking to Fred I actually felt sorry for him. He loved his wife so much that he wanted her to be happy and thought she needed sex.

She told me that she liked sex but she wasn’t one of those women who craved sex. She loved Fred with all her heart and remembered how they talked a lot about sex in their younger days. Fred had always wondered what it would be like to see her with another man.

Lillian said she agreed for a couple of reasons. First was she did wonder what it would be like with another man; but also she was doing it to complete Fred’s fantasy. She also told me that the money would help pay the deductibles on Fred’s treatment. They were lucky to have insurance but still owed nearly five thousand dollars, and the money would help.


The day before we were to get together Bill asked me if I wanted to go to a swingers’ party. I told him I was meeting with my last couple and besides I didn’t have a date anyway. I asked him who he was going with and he laughed. He said Beth, the teeny-bopper we were with last year, agreed to go with him.

Her boyfriend left her the day I had sex with her and then Bill took her home. He went out with her a couple of times but he said it was nothing serious, just sex among friends. I wished him the best and planned my evening with Fred and Lillian.

Lillian was a very nice looking woman. I could see that Fred was very proud of her. We had a nice dinner and Lillian and I had a couple of drinks. Fred just drank water due to his condition. They did tell me that they wanted to keep this date a secret. There was no way that they wanted anyone to know what they were about to do.

I decided to take them to a nice motel in the next town over. I told Fred that Lillian could ride with me and he could follow us. At first he was a bit concerned but I promised him that I just wanted to talk with Lillian and make sure she wanted to do this.

That’s when Lillian told me why she was doing this. I told her I would go easy but I wanted her to try and enjoy it. It might be a bit hard with Fred watching us.

We went to our room, which I paid for the whole night, and we did it a bit differently. Lillian went into the bathroom and put on a nice nightgown. I talked with Fred and told him that I would do my best to bring Lillian pleasure and how much she said she loved him.

When she came out I dimmed the lights as she got on the bed. I lay next to her and Fred sat in a chair watching. I started by gently touching her breasts. She instinctively put her hand over mine but she realized what she did and removed her hand as I began to massage her breasts on the outside of her nightgown.

“Honey, shouldn’t you take off your nightgown?” asked Fred.

I knew she was nervous, but the idea coming from Fred helped, as she sat up and I helped her remove it. As she lay back down I began massaging and kissing her breasts. They were soft but her nipples were beginning to react to my touching. I took my time and continued to suck on her nipples till they were hard.

I lowered my hand to her tummy. casino oyna Again by instinct her hand was on mine. I slowly moved it down to her belly and gently massaged it. I could feel her reacting to every touch now. I slid my hand down on her mound. I noticed she spread her legs for better access.

I slid my fingers down further and found her pussy to be wet. She went to close her thighs, but quickly opened them again. I now slid my fingers into her pussy. She looked over at Fred who was smiling at her. She then opened her legs even wider.

I got down between her legs and kissed her pussy as I fingered it. She was pushing against my face. I knew she was getting hotter. Hardly a word was said but she was making noises. She couldn’t deceive me because her body told me everything. It loved what it was receiving.

I got up but was still fingering her, now with two fingers. Fred spoke again, “Lily, I want to see you suck on his cock like you do mine.”

I looked at her and she nodded ok. I got off the bed and took off my clothes. I think she was a bit shocked when seeing my cock. I told her she didn’t have to take it all, just suck what she wanted.

I lay down and she bent over me and wrapped her hand around my cock. It wouldn’t go all the way around so she used both hands. She started by kissing the head and then slowly took the head in her mouth. She took about four inches in her mouth and went up and down on my cock.

She pulled my cock out of her mouth and said, “Fuck me now, I’m ready.”

She lay down and I got between her legs. I held her legs up while she took hold of my cock and guided it into her pussy. She let out a big moan and then closed her eyes as I began to fuck her slowly. Fred sat there smiling at her reacting to the fucking she was getting. She kept pushing her pussy up against me.

She had taken it all when she had her first climax. She screamed out, “Oh God, it feels so good! I love it, Fred!” She opened her eyes and looked over at Fred. She had tears in her eyes.

Fred reached over and took her hand and held it. I continued to fuck her harder and harder. I pulled my cock out of her and lay behind her and put my cock back in her. It went in very easily. Now she was facing Fred as I pounded her pussy from behind. She pushed her ass back against me as I held on to her hips.

They stared at each other and held hands. I could feel her getting ready for another orgasm. I was ready also as I pushed my cock hard into her and filled her pussy with sperm. She cried out how good it felt. I left my cock in her till I felt her pussy stop having spasms.

Afterwards I got off the bed and pulled the sheet over Lillian. I got dressed and then handed Fred a check for five thousand dollars. I told him that Lillian said that was what he owed on his treatments. She did this for him.

He looked at me and cried. Much as I don’t understand marriages, I believe Fred and Lillian truly loved each other. I left their motel room and headed back home to my own. I didn’t take any videos but I truly felt happy that I might have really helped this couple.

I talked with Bill the next day and he told me he had a pretty good time. He asked me if I remembered Roger and Marsha. They were one of the first couples that I had paid for sex with. Bill told me that they became swingers after being with me.

Marsha loved Roger but needed more. I figured it was a change of life thing. Roger didn’t want to lose her so they decided to go to a swingers’ party once in a while. Bill told me he thought Marsha was a pretty good lay and he was her first black guy. Roger had a hard time keeping up with our teeny-bopper Beth, but he took some pills to help him out.


My life began to change after being with Fred and Lillian. I tried to see things differently. I stopped the pay-for-play with the married couples. I tried to be more positive, and Bill and I worked on getting more customers in our exercise business. The remodeling was almost finished and the gym looked good.

Bill was in charge of hiring of a few more employees. I decided to start remodeling the motel. I also had to start looking for a new desk clerk and bookkeeper.

I bought the motel from Harold and Emma, who had owned it for the last forty years. They were now in their late seventies and they told me, not as spry as they once were. When I bought the motel Harold promised to stay on and run the desk and do the books.

We had a talk a few days ago and he said he was about ready to give it up and he and Emma would be heading to Florida. He said he wouldn’t leave me high and dry. He’d help train a new desk person and go over the books when I found a new bookkeeper. He hoped to move in about two months.

They live in Apt.

, which was right next to the office. I was giving him six hundred dollars a week plus the free room while he worked for me. I also had two women who cleaned the rooms daily and a part-time maintenance man working for me.

I decided to hire the construction canlı casino crew who help build the add-on to the gym. They were local contractors and did a great job. First I was going to have them redo the outside of the motel and then work on each room. I wasn’t going to go overboard but according to Harold the motel hadn’t had any major remodeling in over thirty-five years.

Things were going well and the gym had picked up a number of new customers. Bill pretty much ran it. He did the hiring and firing for the gym. I did go there most every day for a while and I worked out about three days a week. Bill liked being the man in charge and it was a burden I didn’t need. He was much more of a people person than I was.

I was going through my e-mail one day when I got a solicitation for one of the couples sex get-togethers I used to have. I hadn’t posted those ads for over six months. I had to wonder where this person even read it. I was out of the sex business but found myself reading this comment.

“Zack, I would love to have sex with you for a thousand dollars. It has to be this weekend. Please let me know as soon as possible. I really need the money. Thank you, Jenny.”

I was totally surprised to see this. She left her phone number and a picture of a beautiful young woman maybe around twenty. There was nothing sexy about the photo like you would expect. It was a headshot like a graduation picture. Something inside of me wanted to call her. I wasn’t doing this any more but I felt a sense of urgency in the note.

I called her and she seemed surprised that I called back. I told her I was no longer doing the study (I didn’t want to tell her what it really was) but she pleaded with me to talk with her. I told her I would meet her and her husband at the neighborhood restaurant and see what they had to say, but no promises.

I honestly don’t know why I told her I would be there. Maybe it was her picture or her sense of urgency. I really didn’t care about being with other men’s wives any more. Strangely enough, I was looking for a normal relationship.

I was sitting in the restaurant having a cup of coffee when I saw her walk in. She was just as cute as the picture she sent. I was surprised that her husband wasn’t with her and even more surprising she was pushing a baby stroller. At first I thought maybe I got her pregnant but I knew I was never with this woman. I know I would have remembered her.

I waved to her and she came over to my booth. “Are you Zack Hadley?” she asked.

“Yes, and you are Jenny Wells I take it? Please sit down. Would you like a cup of coffee?”

“Yes, thank you. I better start out and tell you I sort of lied to you. I’m not married. There is no husband.”

I looked down at the baby who was sleeping. He was wrapped in blue so I figured it was a boy. “So what is this all about? I also want to know how you read my ad. It hasn’t been posted in over six months.”

She looked very nervous. Her coffee arrived and she took a big sip. It gave me a chance to see how pretty she was but why was she here. She had her baby with her, I presumed it was her child but she did say she wasn’t married.

“Mr. Hadley,” she called me. “I need the money by Monday. I have to pay my rent or I’ll be kicked out of my trailer. I have a month-to-month lease. I’m not a whore or a slut. I’m doing this for my baby. I can’t have him living out of a car, I love him too much.”

“Where did you get my information? I told you it hasn’t been on line for six months.”

“I was crying in the library and a girl at the college started talking to me. I told her I needed to find a job or I would lose my home next week. She told me if I needed some money to contact you. She had some old ad in her loose-leaf binder. She said you paid to have sex with women.

“I told her I could never do such a thing and she told me you paid a thousand dollars but would only be with a woman one time. It was some kind of study you were doing. She also said you weren’t hard on the eyes.

Her name was Beth.”

Our old teeny-bopper friend still had my ad. Isn’t that nice? Jenny seemed to be a nice person, but I wasn’t big into giving handouts or paying a single woman to have sex. Especially a thousand dollars. I decided to listen to her story.

“Jenny, I don’t do the study any more but I would like to hear your story. Maybe I can help you out. I haven’t eaten today; would you like to have lunch?”

She said yes and the waitress took our order. Jenny started to tell me her story.

“I’m from Indiana. I was brought up in foster homes as far back as I can remember. I was told my parents were killed in a car wreck when I was very young. Now and then I get little flashbacks but I don’t know if they’re real. I was lucky enough to get good foster parents but never got adopted.

“I was always quiet but studied hard. I looked at my life and said I was going to make something of myself. After graduation from high school I attended the community college. I was kaçak casino going for a degree in accounting. It would take me two years. I worked part-time at a fast food restaurant to give me a little spending money.

“I received a few scholarships and took out some student loans which I still owe on. Near the end of my first year I met a guy named Brad. He was taking a couple of night school courses. I would stay late in the library and do my homework. One thing led to another and Brad and I got together.

“It was the first time for me and I thought I was in love. We got together maybe twice a week. I was stupid and didn’t use birth control. We used condoms most of the time but not every time and I got pregnant. When I told Brad, he told me he was already married and had a child of his own. He told me he was sorry and gave me five thousand dollars to get an abortion.”

She had tears in her eyes and I told her to take it easy. Our food arrived and we began eating. She would look over every little bit to make sure her baby was ok. After she ate most of her lunch she continued her story.

“At the end of the semester I moved to Ohio and the college transferred my credits. I started the following season at the community college here. I worked all summer putting money aside that I knew I would need. I used two thousand dollars of the five thousand that Brad gave me for the abortion and bought my car. It may not look the best but it serves its purpose.”

“Where did you work during the summer?” I was intrigued with Jenny. She seemed so easy to talk to. I did wonder if she was telling me the truth.

“I worked as a waitress at the Olive Garden. I made good tips but when my pregnancy started to show they weren’t too happy with me. I did work till my eighth month and they let me go. My baby was born pre mature by a couple of weeks. I went to the hospital. They had to take me and delivered my baby. I was so alone.

“After it was all over I now owe the hospital thirty four thousand dollars. They knew it would be like getting blood out of a turnip. I started paying them a hundred dollars a month and they accepted it. They made an agreement with me that as long as I made my payments they wouldn’t charge me any interest.

“I guess they knew that I could file bankruptcy and they wouldn’t get anything. I have been paying my payments for a year now. I only owe them thirty two thousand eight hundred dollars.” She had to laugh after saying that.

“What about college? Did you go back? Are you working anywhere now?” I was really interested in her story. It was the story of a real struggle to survive. I wondered if my Dad didn’t leave me the money, where would I be today.

“I live in the trailer court; it’s pretty dumpy. It was all I could afford. There is a neighbor that I love. Mildred is in her late sixties and offered to watch Jerry for me when I went back to school.”

“Jerry, your son’s name is Jerry?” I asked.

“Yes, I really liked that name. Of course he has my last name too. Anyway Mildred watches Jerry when I attend school. She does it for ten dollars a day. I’m lucky that she will do it for so little. She always tries to help me out. She never pushes me for the money. I’m three hundred dollars behind in my payments to her.

“I found a job in a lounge that I worked weekends and once in a while a day or two during the week. My tuition for college is paid by more student loans. I have one month to go before I graduate. I took off the one semester when Jerry was born. I just need to make it one more month to graduation.”

“So what is the problem now that you need money by Monday? Aren’t you still working?”

“I got fired last month. The night bartender said if I didn’t sleep with him that I no longer had a job. I knew some of the other waitresses had sex with him but I wouldn’t do it. One day he grabbed my ass and I slapped him. He fired me.”

“Couldn’t you file charges or something for being fired unfairly or for sexual harassment?” I asked.

“When I took the job I was paid under the table. I wasn’t listed as an employee. He said I would get more money that way. Another stupid move by me but it did give me more money. I have no way to prove anything.

“As I said, I will get evicted if I don’t pay my rent by Monday. The bastard said he would give me another month to come up with the money if I would sleep with him. God, I can’t stand him!”

“So you wouldn’t sleep with your boss or your landlord but you come here and say you would sleep with me for a thousand dollars. Doesn’t make a lot of sense.”

“They are both pigs. I was at the end of my rope and didn’t know what to do. After talking to Beth I figured it was a one-time thing and could help me make it to graduation. I know it’s something I would have to live with but I would never be seeing you again. Does that make any sense to you?”

“Let’s see. You owe almost thirty three thousand dollars to the hospital. Another fourteen thousand in school tuition. Two months rent and three hundred to your baby sitter. You have no job but hope to get one as soon as you graduate next month with a degree in accounting. You’re also a single mom, does that about sum it up?”

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