Her Little Money Maker

I spoke to her by phone on a chat line and she told me she ran her own escort service. I told her how I was submissive and that I wanted to dress in women's clothes and be a maid and sex slave. I told her I wanted to be forced to be with men. I told her I loved humiliation. I told her all my fantasies. We spoke a few times and she said she wanted to meet me. The first time was in a coffee shop and we talked for an hour about all kinds of things. Mostly she asked questions and I answered. She said she wanted to see me again and would call. I must meet her when she called.

A week later she called and told me to pick her up. We went to a large apartment building and went to an apartment. A man answered the door and we entered. He went to the kitchen and said nothing. She took me by the hand and led me down a hall to the bedroom and closed the door. She told me to take off all my clothes and to not ask any questions. I did as she said. She said her friend was letting us use the apartment for our games. I became very excited as I thought we were going to have sex. I did not speak as ordered.

She told me to lie face down and spread eagled on the bed and then tied me to the four corners. When she was done, she started laughing and said, "Well, I guess you really do want it."

She told me she was leaving and I had better be good because she was taking my clothes and wouldn't bring them back unless the man in the other room phoned her and told her he was satisfied. She gathered up all my clothes and left the room. I heard murmurs from the other room as they spoke. Then I heard the front door close as she left.

A few minutes later the man came into the room and walked around the bed staring at me without speaking. He began to rub me and said, "I had better be good or this could be very painful". He asked if I had ever been with another man and I told him no. He said that was fine and not a prerequisite as I had all the equipment and holes to satisfy any man. He began to take off his clothes and was smiling the whole time.

He told me I must have known what was going to happen and by letting her tie me up I was consenting to it in his eyes and anyone else's. He asked me if I wanted him to use lubrication or not. I said, "Yes, please." He said the only way he would use lubrication was if I sucked him off first. I agreed. He then asked about a condom. I said yes again and he said I would have to swallow all of his cum or no condom. I agreed.

When he was ready he sat at the head of the bed with his legs on either side of me and his hips at my face. My mouth was positioned over his cock which was just starting to get hard. He told me to work at my own pace and no teeth. If I missed a drop and didn't swallow, no condom. I lowered my lips, opened my mouth and began.

I sucked him for quite a while. I could feel he was holding back. He called me a good little whore and cocksucker. He set the pace with his hand behind my head. I worked very hard to please him because I knew I had too. He finally came and I swallowed all of his cum. He got off me laughed, rubbed my ass and said, "I'll be back later." He left the room and closed the door.

About two hours later he came in and checked my bonds. They were taut but loose and I had good circulation. I could still taste his cum in my mouth. He was still smiling and laughed at me for getting myself into this situation. He sat on the side of the bed and rubbed my ass. He said, "Now we make you a boytoy."

He took out some K-Y lube and began to finger my ass. It was not too painful as he was very gentle. He did this for 15 minutes and then began using another finger and finally a third. After a half hour he stood and had a huge hard on. He put a condom on. I could see in the mirror beside the bed as he mounted me from behind. I could feel his weight on the bed. He inserted the head and pushed slowly forward. It hurt more then the fingers and I cried a bit. He spoke softly to me but he was laughing at me all the time. When he was all the way in he held it there.

After a bit it didn't hurt so much. He began to slowly fuck me in and out. After a few minutes it began to feel really good and I got hard. He reached under me and stroked my cock saying, "A fag is born." He began to fuck me harder and harder. Again I could tell he was holding back. Finally he came and just held inside me. As he came I came too. He rubbed my cum on his hand and made me lick it off. After a few minutes he laughed and left the room.

About an hour later I heard a knock at the door and voices. She came back into the room alone and took some pictures of me with her Polaroid. "No longer a virgin, little man. Now we know you are fuckable."

She untied me and told me to get dressed and come out. I dressed and went into the living room. She told me to remain standing. They were both seated and talking. He told her in detail everything we had done and how much he had enjoyed it. He then counted our $150 and gave it to her. He said I deserved something extra for working more on sucking his cock then he expected and gave her a $50 tip. He told her I must really like sucking cock because of how much I got into it.

She thanked him and we left. In the car she counted out all the money and told me I had been a good boy but as her slave I didn't deserve any money. I had been tied and just a hole to be fucked. She did all the work setting it up and therefore the money was hers. Besides she said I seemed to have enjoyed it too much. She had me drop her off and I went home.

A few days later she phoned and said she wanted to see me again. She reminded me of the Polaroids she had of me and said to pick her up in the same spot. We went back to the same apartment building and I began to back out. She was very soothing and told me I didn't have to do anything I didn't want to but she wanted to use the apartment and the man owed us a favour for last time. She said we would be alone and she would dominate me.

We got to the apartment and she opened the door with a key. There didn't seem to be anyone here. She sat on the couch and told me to strip completely. I did. She told me to go into the bathroom and shower then report back to her. I did.

When I returned wearing a towel, she was standing by the door with my clothes in a bag. There were two men sitting in the living room. One was the man from last time and someone new. They all laughed when they saw me. She said, "I will be back in the morning if they call and say you were good". She told me not to look so sad. I wouldn't be doing anything I hadn't already done and laughed as she left.

The two men came toward me saying how sexy I was and how much they were going to enjoy this. They pulled my towel off and I loudly said stop. The man from last time told me to go ahead and yell for help. Someone would call the police and I could explain how I came to be in the apartment with two gay men naked and I wanted to leave. He said he hoped they didn't call the newspapers.

I looked shocked and he laughed as he said that if I went along with everything it wouldn't hurt and I might enjoy it. He said I only had to suck their cocks a few times and let them fuck me and in the morning I could leave. They were both feeling me up and I was starting to get hard despite myself. I softly said okay and they led me to the bedroom. I spent the night in bed with both of them mostly with a cock in my mouth or up my ass. I cried but they continued to use me and laugh at me and my situation saying I let myself get into it and I deserved what I got for it.

In the morning they called her back and she gave me my clothes to put on in front of all of them as they told her in great detail how I had been used. They paid her and we left. She showed me the money and told me again it was all hers.

A few days later she called and told me how bad she felt for using me. She said we had our fun and she had made some money but she was feeling guilty and wanted to make it up to me. She said she was going to a party and wanted me to come with her. I agreed because I thought now she would have sex with me.

We went to a house and I could hear the music from the street. We were both dressed up. A man let us in and the party was in full swing. I got us both drinks and she disappeared downstairs for a few minutes to the rec room. When she came up she looked like the cat who had eaten the canary. When I asked to go downstairs she said later for that. We spent the night with her introducing me to everyone. They all paid a lot of attention to me and asked me lots of questions about myself. She kept my glass full for a while and I was feeling pretty good. I did notice some odd things after a while. There was loud music but no one was dancing. People kept going downstairs for a while and when they came up they all had smiles on there faces and were looking at me funny. One woman burst out laughing when she saw me.

The girl kept getting glances from everyone when we were talking as though they all shared a secret I was not in on. I also noticed there were only a few women and mostly men at this party. We had been the last to arrive and everyone seemed to be waiting for something. After a while, the man from the apartment came up from the basement and said to her it was time. I was shocked to see him. Everyone in the room was now staring at me with wide grins on there face. She said, "Okay I just have to prepare him. Give me a minute."

She took me by the hand to the stairs. Halfway down she stopped with a big grin on her face and stared into my eyes. "I want you to remember I know where you live, where your parents live, where you work, everything about you. If you want to keep your private life private you better be good." She then pointed into the basement where I could hear moaning. There was no music down there and everyone was watching a large screen TV with a tape playing. I was on the tape. The woman who had laughed earlier saw me, pointed at me and laughed louder.

The tape was of my two previous encounters and showed me sucking and fucking men. She held my hand tight and said not to panic. "Everyone here is understanding and will keep quiet. I will give you the only copy of the tape and no one will ever know. After this party I will not bother you again but for tonight you are going to earn me lots of money and give my friends lots of laughs."

With that she pulled me down the stairs and across the room into a bedroom and closed the door. I was in shock. She started taking my clothes off and told me if I didn't struggle and satisfied everyone I would not get gang banged in the ass. Any sign of trouble and the guys would tie me and fuck me all night long. She said I had to suck off every guy there while everyone watched. At the end of the night my ass would be raffled off as a door prize and I would be fucked. Then I could leave with the tape. Any trouble and I would be gang raped, videoed and both tapes would be sent to my parents, friends and work.

When she finished saying this I was naked. I was in shock and just moved like a zombie. She was smiling and giggling the whole time. She then kissed me on the cheek and whispered in my ear "I hope you fight. I would love to see you ass raped all night." I quickly said no I would obey.

She laughed again and held up a set of handcuffs. "No hands when you give head. No condoms and you swallow every drop. Anything you miss you lick up. The girls are in on the draw and we have a huge strap on dildo if one of them should win. Have fun boytoy." Then when I was cuffed she began stroking my cock. When it was hard she used it like a leash to pull me out into the rec room.

Everyone from the party was there. The lights were all off except for a spot light on a mattress they had put in the centre of the room. The men were all stripping or naked and the women stayed clothed and watched. She led me to the mattress and I knelt on it. She sat back with a drink and one of the girls came over to her and they kissed. Then they both looked and me and laughed. She said "Make some money bitch."

I spent all night sucking and swallowing. My lips were raw, my tummy full, my knees ached and I couldn't completely close my jaw when it was done. The winner was the girl who had come up and kissed her. She was the same one who had laughed before. She held a 12 inch dildo and had a huge grin. She striped, strapped it on, lubed it and said "Let me show you how it's done boys." She fucked me very hard and I couldn't walk very well after. I passed out.

When I woke I was in bed with a man who said he paid extra to take me home. He said I had been out of it for two days. He drove me home early Monday morning. When I got to work there was a note from another department in the company for me to go to a meeting. When I got to the office, the secretary had her back to me. She said that her boss was out for the afternoon but to go into the office.

I went in and when I turned and looked at the secretary she was laughing and said what a great fuck I was. It was the girl who won the door prize. She handed me the tapes and said her friend asked her to return them to fulfill her part of the bargain. She said, "Of course now that you are no longer hers, I took the liberty of making copies for myself this weekend. Now you are mine."

Part 2

I could not believe the evil smile she had on her face as she walked toward me. I was frozen and my mouth hung open. "Tch. Tch." She said and she pushed my mouth closed with her index finger. She walked passed me to her boss's desk and sat down. I was stunned.

She told me to have a seat in front of the desk and we would discuss the ground rules. I was to call her Miss Sharon at all times. I was to obey all of her commands without question. She knew who I was and since we worked for the same company, she had found out my parents address, all my friends and her boss and mine were very good friends. She laid all of this our and told me I should watch the video of myself because that is what everyone would see if I didn't obey.

I hung my head and said I would do anything. I begged her to please let me out of this nightmare. She asked me how it had happened and I told her. She laughed at me again with that loud laugh. I was afraid someone would hear her. She told me that we may as well get things started as she had no intention of giving up her little windfall.

She told me to go lock the door and take off all my clothes so she could see what was now hers. I did as she said and stood in front of her behind the desk where she motioned me. Without words she pointed down and I kneeled. She grabbed by hair and pulled forward as she pulled up her skirt and I knew without being told to eat her. I did this for a long time until I felt her shudder.

She pushed me back and straightened her skirt. "Put these on." She handed me her pink panties. "Now get dressed and leave your underwear. Go back to your office and in one hour you will go to the men's room. I want you to strip in the stall to your panties and wait for a man to come in. He will get in the next stall and you will take off your panties and hand them to him. You will wait until he leaves, get dressed and leave the men's room. Go to your desk and wait for my call."

I left shaking. I was not sure what to think. I went to my desk but I couldn't get anything done. When one hour was up I went to the men's room. There were two guys in there talking and I went into the stall. I took off my jacket, tie and shirt and waited until they left. Then I took off my shoes and pants. I hear the door open and someone went into the other stall. I took off the pink panties and handed them under the stall. A man laughed and said, "I don't believe it." He took the panties and left. I quickly dressed and left as well. I saw a man talking to Miss Sharon when I left and shaking his head yes to her. She smiled at me and wiggled 'hi' with her fingers. I hurried to my desk.

I got the call a few minutes later from Miss Sharon. "You will go right now to the storage room and when you get there you will go in and lock the door. Do not turn on the light. Take off all of your clothes and kneel. When that is done say 'ready' out loud. The gentleman from the bathroom will then stick his dick in your mouth. You will suck him until he cums and let him cum in the panites he has. He will then help you get in them and then leave. You will finish dresssing and wearing those wet panties, come to my desk." She hung up.

I did as she told me. I didn't even know where this man worked or who he was. When I was finished, I went to her desk and she had me open my pants and show her my wet panties. She laughed again and I zipped up quickly before anyone came. She said, "I'll bet your heart is just beating faster and faster." I said it was. "Good. That means you are very obedient to do this at work and that you know my threat is real. The man you just sucked off works across the street and doesn't know who you are."

"My boss is looking to give me a big raise soon. I want you to know that you are going to help me in making sure that it happens today. I know you can serve men and women now. That helps a lot." She then took my hand and led me into her bosses office. The office was different now. There was nothing on the desk except leather straps tied to the four corners. She attached me by tying me face down on the desk spread out and greases my ass a bit. Then she stuck a dildo with a long handle on it.

It hurt a bit going in as I was still sore from the weekend but it went in pretty easy. She giggled and told me I was a good boy. She said that I was to call her boss Ma'am and not to say anything unless I was spoken to. She then place a mask over my face and left the room. I was like this for an hour.

I heard the door open and Sharon's laugh as she told her boss to enjoy. Her boss said, "So you are the gigolo that Sharon thinks will win her a big raise today. You better be good boy." She grabbed the handle of the big dildo and jiggled it up and down, sideways and pulled it out slowly until it was almost out. The she slowly slid it back in as I groaned. "Quiet." She said as she slapped my ass hard. "I demand respect."

She laughed and told me that today would not be too demanding but that she wanted to know I was obedient. She started to rub the backs of my leg and then my back. She rubbed my ass cheeks. She then began working the dildo in and out of my ass. Slowly, quickly, soft, hard. Just like a test drive she told me. She said she didn't want to get dirty as she had a meeting soon so play would have to end. She made me suck her fingers like a cock to show her I knew how.

Then she called Sharon in. She told Sharon I would do but how did she expect to get a raise if it was going to cost her money to have this gigolo. Sharon smiled and handed her the remote control for her TV and VCR. The woman pushed on and play and saw me getting put through my paces. They both laughed and Sharon told her, "you ain't seen nothin' yet." Sharon pulled off my mask. Her boss started to laugh hysterically.

"Well I guess a free gigolo is worth a big raise. You got it." She told Sharon to get me back to work after some pictures on her desk like a trophy. Sharon took the pictures and untied me. She told me to put in a small butt plug. To keep me loose. I was to get back to work and stay late for a few hours to make up for my play time. Then I was to go home and wait for the boss to call me. "I hate to lose my little money maker but I know I will get you back someday. Until then, have fun. Ha Ha Ha Ha Ha."

I had no choice. I did as I was told.

 

You can also leave feedback & comments for this story on the Plaza Forum

03.10.15