Chapter 1

I was sitting at a table in the student cafeteria eating lunch and reviewing the notes I'd taken during Mallory's Business Law III when someone pulled out a chair and sat down across from me. I looked up and into the most startling blue eyes I had ever seen. They belonged to a girl I'd never seen before. Actually she wasn't a girl, she was a woman. I'd guess maybe twenty-four or twenty-five.

"Harold right? She asked.

"No" I replied, "Its Herman."

"Sorry. I'll have to thump the person I got my information from. I wonder what else I got wrong from my source. May I call you Herm?"

I nodded my head yes and she said, "You are a Business Management Major, you live in the dorms, are here on a half a dozen scholarships, work in the school cafeteria for spending money. Again, right?"

"Not completely. I don't live in the dorms. I have a house. The rest of it is right."

"No car and don't have enough money to date much. That about right?"

I nodded another yes and then asked, "Who are you and what is this all about?"

"My name is Samantha and I want to offer you a job."

"What kind of a job?"

"An actor in a porn flick."

"What?!!!"

"You heard me right. An actor in several porn films with me. They are specialty films and as such they require a certain feel to them and you are perfect for what I need. I'll need you maybe two nights a week for about six weeks and I'll give you five hundred a week. Think about it. I have a one o'clock in the Harris Building so I have to run, but if you are interested meet me at O'Malleys at seven tonight. Hope to see you there" and she stood up and left.

As she walked away I scoped out her marvelous ass as I rolled the "I want you to act in several porn films with me" in my mind. I hadn't been laid in a year and the though to of me being buried in that ass, even if it was being filmed, did appeal to me.

She disappeared through the cafeteria doors and as I turned back to my lunch and my notes I wondered who the asshole was who was playing jokes on me. I put it out of my mind and concentrated on my notes on contract law.

Even knowing that I was going to be the butt of a practical joke I still showed up at O'Malley's to see what the next part of the joke would be. I walked into the place expecting to see half a dozen of my friend waiting for me with big smiles and waiting to say "Gottcha" and laugh. I didn't see a soul that I knew except for the girl who said her name was Samantha.

She was alone in a booth toward the back and there were no people in the booths around her. As I took the seat across from her she smiled at me and said:

"You came. Does that mean you are interested?"

"To be honest I'm here because I was thinking that I was being set up for a practical joke and I was curious to see what the next part of it would be."

"No joke Herm. I was dead serious about what I said to you in the cafeteria. I need some one just like you to work with me in a series of porn films."

"Some one just like me?"

"No lies here Herm, and I don't want you to take this wrong, but you have the look that I'm looking for. You are attractive enough to have drawn the attention of a girl like me, but you also look a little on the wimpish side and that's what I need. A guy that it would be reasonable to believe that he could have a girl like me, but who also looks like he could be bossed around. Pussy whipped I believe is the term used."

"Pussy whipped?"

"Have you heard the term "cuckolded husband?"

I nodded a yes.

"There is a big demand for cuckold type photo galleries and films. I can give you the addresses of a dozen sites that follow that genre. I want to make a series of those types of films and galleries and I need some one to play the part of the cuckolded husband."

"You want to pay me five hundred a week to pretend to be your husband and fuck you?"

"No Herm, I don't want to mislead you on this, but I'll be paying you to act as my husband, but you won't be fucking me."

"I don't understand."

"You do know what a cuckold is right?"

She saw from my facial expression that I wasn't sure so she went on, "One definition of a cuckold is a man who knowingly lets his woman fuck other men. A good cuck will watch and even help out."

"Help out?"

"Guide the other men's cocks into his wife. Clean her out after it is over."

"Clean her out?"

"You know; go down on her and suck all the goo out of her."

"Sorry. Don't think I can do that."

"You don't have to. That's why it is called acting. You get down into place and then the camera is positioned so that it looks like you are doing it."

"I don't know. It doesn't sound like something I could do."

"Sure you can. You will do maybe four hours worth of work and get five hundred. That's one twenty-five an hour and you can't beat that with a stick."

"I still don't understand what I'd have to do."

"Basically you stand around looking like a wimp while I treat you like my personal servant. I'll give you an overview of one of the first films in the series. You are having a poker game at the house. I was supposed to go out for the night, but things fell through and I decided to stay home and act as hostess. A couple of hours into the game and after every one has had several drinks one of the guys will say something like "You look good enough to eat Bonnie." Bonnie is my screen name and I'll say something like "You any good at it?" The guy will say that he has never had any complaints and then I'll say that I'm just going to have to see for myself."

Every one at the table will look at look at you and then I'll say, "Bobby won't mind, will you honey?" Bobby is going to be your screen name by the way. You will look like you want to puke, but you will say something along the lines of "Of course not dear. Whatever you want" and the guy and I will leave the room. The other guys at the table will say things like, "She do this often?" or maybe "You let her get away with shit like this?" You will mumble something like "I can't stop her." They will look at you disgusted and then the camera cuts to the bedroom where me and the guy are getting it on.

One by one the other guy's will leave the table and come to the bedroom to watch. Then they will start asking if they can join in and I'll say "Maybe next time. I'll need a little time to prepare Bobby for it" and that will set up the next film in the series."

"And I get five hundred for just that?"

"And you will have to pretend to be cleaning me with your mouth when the fucking is done."

"Just pretend right?"

"That's all Herm, just pretend."

"When would this start?"

"Next week Tuesday if you say yes. I'll get together with you Monday and go over the script so that we can hit the ground running on Tuesday. When can you let me know yes or no?"

"Right now. Count me in. One thing though. This is all under the table right? No taxes or any of that crap."

"You'll get the full five Herm. In cash. Let's exchange phone numbers so we can stay in touch."

"I don't have a phone. You will just have to catch me here at the cafeteria" and I gave her my work schedule.

"Maybe when you get your first five hundred you can get a cell phone."

"I would like to know something."

"What?"

"Just who you were getting your information about me from."

"You will see on Wednesday when you show up for filming."

"So I know him then?"

"Yes you do and I think you are going to be surprised."

"Why?"

"Think of every one you know and then try to figure out which one might be working in porn." She stood up and said, I'll catch you Monday. See you then."

As she walked away I did what she said and tried to think of who I knew that might do porn films and I couldn't think of a one. Then I smiled as I thought how many of them would have ever figured me for a male escort. Thinking of that took me back in time to a place where things had been a whole lot better.

I never knew my father. He caught the wind the day my mom told him that she was pregnant and she never saw him again. She went to work and raised me as a single mom.

We never wanted for anything. We had a nice home in a good part of town and mom always had a new or fairly new car. She traded her old one in every three years. She always had nice clothes to wear and so did I. She told me that she worked in an office as a personal assistant to the owner of the company.

I guess she didn't miss my father all that much, if at all, but she never married. She did date a lot, but I guess no one caught her fancy.

I was your typical kid. Ran around with my friends, played sports and chased girls. I was a better than average student and I lettered in football, baseball and basket ball. Mom gave m a good allowance and life was good for me and the only bad spot was when my appendix ruptured and I ended up falling back a year in school.

The day after my eighteenth birthday I found out what my mom did for a living. It was one of those spring days when spring fever grabbed you by the throat and knowing that mom wouldn't be home I skipped school and went home. I'd been there maybe an hour when the phone rang and without thinking "Hey, you aren't supposed to be here" I automatically answered it.

"Hello?"

"Is Jan there?"

"No she isn't."

"Who are you, her manager?"

"Her manager" I said and it was supposed to have come out as a question, but to the caller it must have sounded like a statement.

"This is Tony B and I need her for the day on Thursday. There will be two of us and Carl is really into anal sex. I know Jan charges extra for anal so make sure that she knows. Tell her nine at the Four Seasons in the restaurant. Whoa, I didn't ask. She is free for Thursday right?"

"Yes sir, she has nothing scheduled for Thursday" I said not knowing if she did or didn't. He said goodbye and hung up.

I sat there as the call bounced around in my head. Mom charged extra for anal sex? That could only mean one thing. My mom was a prostitute! The next thought wasn't one of disgust, dismay or even disillusionment. I looked at the house and what we had and the new cars and thought:

"She is a prostitute, but she must be a damned good one to make the money that gave us the standard of living that we had."

I was no different from any other teenager with raging hormones. My mom was a sexy looking woman and I had accidently seen her naked a couple of times and the sight of her naked body had fueled many a masturbatory session and like a lot of other guys I'd even entertained the thought that I'd like to make love to my mother. The thought of my mom taking Carl in her ass gave me a raging hard on and I took my cock out and stared beating my meat as I imagined mom on her hands and knees sucking Tony B's cock while Carl was pumping her ass.

I was sitting there, eyes closed, imagining and whacking away when I heard:

"My God Herman; what's gotten into you?"

I opened my eyes and saw my mom standing there looking at me. If it had been a minute or so earlier I would have dropped my cock and hastily tried to cover up, but I was a nano-second from getting my nut and there isn't a guy alive who doesn't know that at that time all that counts is the release. Your mind at that exact instant in time isn't all that clear either and it isn't working all that well. When I heard "What's gotten into you?" I said without thinking "You" and just as I said it I came and I'll swear that it went a foot straight up and then of course what goes up must come down and it did all over my lap.

My mom stood there looking at me stunned. "Me? You were doing that because of me?"

I still wasn't thinking clearly and I said, "You and Carl."

"Me and Carl? Who is Carl?"

By then my mind was starting to think a little more clearly. I realized that Tony B, whoever he was, would sooner or later talk to mom and she would find out about the phone call so I figured that I might as well tell her. When I was done she shook her head and I could see that she was about to cry.

"You were never supposed to know. Oh my God; you were never supposed to know. Whatever are you going to think of me now? And jerking off to an image of me and some guy named Carl who I don't even know. "Oh my God!" And she ran off to her bedroom crying.

I cleaned up my mess and then headed to my room. As I passed mom's room I heard her still crying and, doing something that I had never done before, I went into her room without knocking. She looked so pitiful lying on the bed sobbing that I got on the bed with her, took her in my arms and held her. She cried into my shoulder until she was all cried out and fell asleep. I eased away from her, covered her up and went to my room.

The next morning mom was in the kitchen making breakfast when I got up. When I walked into the room she pointed at a chair and said "Sit!" I sat down and she said:

"I'm sorry that you found out about me. I never intended that you would know. Now that you do know I have to make a couple of things perfectly clear to you. I am not ashamed of what I do. I've made a damned good living for us doing it. The second thing is that even though what I do may make you think less of me and lead you to believe I am some one with low or no morals there are lines that I will not cross. Yesterday when I caught you doing yourself you told me that it was because of the image of me having sex. Get that thought out of your head. You can imagine having sex with me all you want, but it is never going to happen! You are my son and I love you to death, but not in that way. Never in that way! Are you clear on that?"

"Yes ma'am."

"That out of the way I supposed that you have some questions for me. Ask them and I'll do my best to answer them."

Of course I had questions. Why? When? How long had it been going on? I sat there and listened as she told me the story.

She was in love with Charlie Snyder and they were going steady. They were seniors in high school and Charlie had said he was going to marry her when they graduated. He convinced her that since they would be getting married anyway they could start making love immediately. Mom got pregnant, told Charlie and two weeks later he was gone and his parents wouldn't talk to her.

She finished high school, had me and my grandmother baby sat while mom found a job. I was a year old when my grandparents went to a party one night and they died in an accident on the way home. Grandpa got drunk at the party, ran a red light on the way home and got t-boned by a beer truck. There was just enough insurance to bury them. Mom couldn't afford to keep up the house payments and the bank foreclosed.

Next she lost her job, fell behind on her car payments and apartment rent and was a hairs breadth away from being evicted and having her car reposed when the apartment manager offered her a deal. She could pay for the apartment with sex and he had friends who would pay well for a hot looking young chick. Mom was desperate so she took the deal. She did well at it and in a year she had paid off her car and had money in the bank.

One of her customers asked her to go to a party with him and she met a man there who knew what she was doing and asked her why a hot number like her was hooking out of her apartment instead of working as an escort and making much better money. He put her in touch with a man he knew who had an escort service and she went to work for him. In two years she had an established following and was constantly booked so when the owner of the service had a heart attack and died she struck out on her own She had more than enough repeat customers to maintain her standard of living and she was always getting referrals from her steady customers.

Mom told me that we were financially well off and that she had plenty of money set aside to pay for my college education. Then she asked if now that I knew what she did did it change my view of her. I told her no, and that in fact all that it made me think of was that I could never be one of her customers. She gave me a funny look when I said that, but didn't say anything.

Nothing changed between us other than I was now aware of what she was doing when she was at work that I wished I could also be doing. Not fucking her, but fucking. I was still a virgin and it didn't seem to matter how hard I tried I couldn't get rid of my cherry

One night, about six months after mom told me her story I was at home and horny. Mom was on 'a date' and I didn't expect her back for a couple of hours. I was sitting on the couch beating my meat when mom walked in on me. She looked at me, shook her head and said:

"I hope you aren't thinking of me while you are doing that."

The truth was that I was thinking of her. I'd never gotten the picture out of my mind of her that I had gotten after the phone call from Tony B. I still saw Carl pounding her ass while she sucked on Tony B and I whipped off to it a couple of times a week. I knew it made mom uncomfortable thinking that I was jacking off to her so I lied and told her I was fantasizing about one of the cheerleaders at school.

She asked me why I jacked off so much and I told her that until I could finally get rid of my cherry that whacking off was my only sexual relief.

"You are still a virgin?"

"I'm afraid so."

"But why? You are a good looking young man and I was sure that you were getting plenty."

"Don't know ma; I just can't seem to get a girl interested."

"I never would have guessed it. Well, we can't have that. We will just have to do something about that."

I smiled and waited for her to start taking off her clothes, but it didn't happen.

Two days later when I got home from school she sat me down and said:

"I'm going to ask you to do something that you are going to think is weird. I want you to go on a double date with me."

"A double date? I don't understand."

"I have a client who always comes to town with his wife. She goes off to find a sweetie for the night while Bob and I do our thing. They are coming to town and I want you to take care of Linda while I take care of Bob."

"You can't be serious."

"Of course I am. I've already talked to Linda and she knows that you are a virgin and she can't wait to get her hands on you."

A chance to lose the hated title of virgin? And it was set up by my mother? How hinkey was that! Of course I said yes.

"When?

"Tomorrow night. We will meet them in the restaurant at the Hilton at six-thirty. Sports coat and tie. Okay?"

They were already there when we arrived. I was introduced to Bob and Linda, but not as mom's son. I was supposed to be the kid from next door who had the obvious hots for her, but she was too friendly with my parents to do me. Later Linda told me that mom said that I had confessed my virgin status and almost begged her to take my cherry. One night Linda had told my mom that she was tired of the hit or miss bar scene and she just wished she could find some hot young stud she could 'go steady with' when she was in town and that's when mom told her about me. Like I said, I found that out later.

As we were introduced I saw that Linda was about mom's age and that she was a sexy looking lady. I wondered why her husband wanted to fuck other women when his wife was to die for. Whatever, she was going to cure the malignant disease I had. You know, virginity.

We had a pleasant meal and mom and Linda chatted about girl type stuff while Bob and I talked sports. After coffee and dessert Linda said:

"You two have fun. Herm and I need to be going."

She stood up and offered me her hand. I looked at mom and she winked at me. I stood up, took Linda's hand and she led me to the elevators.

I can't even begin to describe the trip to paradise that Linda took me on that night. She had me undress her slowly and then she undressed me. She told me not to be embarrassed because the first couple of times would be quick, but my recovery time would also be quick. She went to her knees and sucked my cock and I'm embarrassed to say that I was indeed quick. She swallowed my output and as she stood she said:

"That got the first fast one out of the way. Now I'll show you how to return the favor when a girl does that for you."

She led me through how she liked her pussy eaten and cautioned me that other women might like it done differently, but what she was giving me was the basics.

"If you want to impress them ask them what they would like and don't just munch down."

After several minutes of eating her pussy (and I will admit to some trepidation when she told me I had to eat her – guys didn't really do that did they?) she said she was ready. I mounted her and then started slamming into her, but she stopped me and told me to slow down.

"Take it easy and go slow at first and then pick up speed after both of us are settled into a rhythm."

Again, I came too fast, but she told me not to worry and that it would get better. And thank God that it did. We went four times that night and the fourth time lasted almost fifteen minutes.

I met mom in the coffee shop at six and as we had breakfast she asked me how things had gone and I told her that I hadn't wanted to stop. She smiled at me and said:

"Maybe you won't have to."

"What does that mean?"

"We'll see."

When we got home mom handed me five one hundred dollar bills.

"What's this?"

"I don't do it for free kiddo, and you aren't going to either."

"Five hundred for doing what I would have been willing to pay to do?"

"With any luck sweetie that won't be the last. Linda and Bob will be in town for another two days. I won't be seeing Bob again, but Linda wants to see you again on both days. Are your grades good enough that you can miss two days of school?"

I was wrung dry when Linda left town. She taught me cowgirl, reverse cowgirl, doggie and what she called the rear leg lift. We did anal and sixty-nine, but I balked when she wanted to try water sports. Luckily she didn't hold that against me. She spent a lot of time teaching me how to treat a woman properly and it was to stand me in good stead.

A week later mom asked me if I wanted to have a date that night and of course I said yes. Her name was Helen and she was close to fifty and I guess she was apparently happy with me because before the night was over she told me that she would be using me more often. I also found out from her that she thought that I was from an escort agency that she and her husband often used. I came to realize that my mom was the agency she was referring to.

From then on mom set me up on the average of once a week and I never got less than five hundred dollars for doing what I would happily done for free or even have paid for. I saw Linda on the average of once a month and once she even offered to set me up in an apartment to be her full time boy-toy and while I was sorely tempted I didn't want to move to Chicago.

Things went great for over a year and then disaster hit me. Mom was run down by a hit and run driver and died at the scene. So there I was at nineteen and a half still a senior in high school and orphaned. I had no other living relatives and I was totally on my own.

I had to make the arrangements for my mom's funeral and all of that. I didn't think I needed to worry about money because mom had led me to believe that we had plenty. She had told me that we had enough to carry me all the way to a PHD if that was what I wanted and the house was paid for, but when I started digging I couldn't find it.

I did find that she had set me up with a trust fund that would pay me five hundred thousand when I turned thirty, but there wasn't much else. She had thirty-two hundred in savings and eleven hundred in checking, but mom had no will that I could find so I ended up having to hire an attorney to get me access to her accounts. She had a ten thousand dollar life insurance policy in my name and it took all of that plus the four thousand that I had saved up to buy a car to pay for mom's burial expenses.

I thought that I'd come out okay because I would have mom's car, but that didn't work out either. I found out that she didn't buy a new car every three years – she leased cars. Mom's car had to go back to the dealership and I even owed some fees on it.

When the dust cleared I had my name on the house and six hundred in the bank. The lawyer's fees ate up what was in mom's checking and savings accounts. My career as a male escort was over because it had all come through mom. Basically I was stone broke. I was able to start college because I had scholarships and I was able to get a job in the student cafeteria that included my meals. I put the house up for sale, but because of the economy it wasn't moving.

Samantha's offer of five hundred for acting in her movies was a godsend.

Samantha caught me during my shift at the cafeteria and we arranged to meet Monday after I got off work. She handed me several pages stapled together and it wasn't quite what I expected. I was expecting a script that described each scene complete with dialog, but what I got was a description of what would be going on. The dialog was strictly ad lib according to the circumstances and situation.

"Is this it?" I asked.

"What did you expect? This isn't some Hollywood big budget epic. It's a fuck film and all that the people who are paying to watch it or buy it want to see is a sexy looking slut taking some dick. I try to make it look real instead of fake, but that's as far as I go."

She went on to explain what would happen and what I would be expected to do and say. My dialog was going to be "Yes dear," "Whatever you say dear" and "Whatever you want dear." I was to say it with a hang-dog look and that I should try and make it look like even though I was agreeing I was hating it.

She ran through how the series was going to go and then she told me that if the series went as well as she hoped she might add to it and I could have even more pay days if I wanted. She gave me an address and told me to be there by six and I told her I couldn't make it before six forty-five because my shift at the cafeteria wasn't over until six-thirty. She thought for a minute and then said that six forty-five would work.

When I got to the address I found that it was a private residence. I rang the bell and Samantha answered the door. She was wearing nylons, high heels and a bathrobe.

"Good. You are here and we are ready to shoot our first scene."

She led me into a large bedroom where there were several people and a couple of cameras set up.

"This is going to be different than what I told you about. The guy for what was supposed to be shot tonight had something come up and he couldn't make it. We will do his scene tomorrow and do the poker game tonight."

She took off the bathrobe and I got instant wood. She was incredible! Firm tits that stood out from her chest like the heads of torpedo's and tipped with nipples that looked to be about an inch long. Her shaved pussy looked mouth-watering and I was immediately sorry that I wasn't going to be one of the guys fucking her.

"This is the last scene in the second of the series. Abe has just finished fucking me and I've called on you to do your duty and clean me out with your mouth."

There was a bowl of stuff on the dresser and as she picked up a turkey baster she said:

"This is a mixture of KY lotion, egg whites and cornstarch. It looks just like cum."

She filled the baster, lay down on the bed and put the baster inside her pussy and pumped the baster's contents into her. She pulled the baster out, handed it to one of the guys in the room and then squeezed her muscles until some of the stuff ran out of her. It did look like cum leaking out of her pussy.

Ignore the camera's Herm. Just pretend there is no one but the two of us here in this room. Can you do that?"

"No problem."

I could say that and mean it because I was used to having people watch me. Bob used to like watching me and Linda and in fact he did do a lot of what I was going to pretend to be doing with Samantha.

"We ready guys? Roll them."

"Rolling" the two guys with the cameras said and then Samantha called out "Get in here Bobby" which was going to be my screen name. I walked up to the bed and Samantha smiled up at me.

"He fucked me good Bobby. He came a lot. See?" she said as she spread her legs and pointed to the mixture running out of her. She drug a finger through it and held the finger up to me. "Taste it Bobby." I hesitated and she said, "I said taste it Bobby" in a forceful tone. With obvious reluctance I bent my head, took her finger in my mouth and as I sucked it clean Samantha said:

"That's a good boy. Now do your duty Bobby."

I let go of her finger and stood there looking down at her. I made no move to do what she wanted.

"Don't make me ask you again Bobby. You know what I expect. Now do it!"

"Yes dear" I said as I got on the bed. Still I hesitated and she grabbed my head and pulled it down to her pussy and said: