Lessons Ch. 01

Through high school I mastered the art of masturbation. I began with sexual thoughts, dirty magazines, pocket books, videos and went from boy/girl sex to boy/boy sex/ boy/girl/boy sex, group sex, kinky sex, finally many many thoughts of bondage and sexual slavery.

The weird part happened in my first year of University. I was heavily into reading sex stories and loved those of control (or rather the loss of control), slavery, bdsm, etc. The etc being everything kinky I had ever heard about. I wanted to move these thoughts and jerking off to the next level.

I had no way to approach this due to my sexual awkwardness. I saw ads in the newspaper and thought maybe swingers would be my way in to kinkiness. So began my letters and then my ads.

I wrote many letters at first to the ad boxes and only had two replies. One was to a couple who send me their phone number. He was very kinky, she was very sexual but not so kinky. He was not home when I called. I spoke to her and she was a bit freaked by my letters. They were true and experienced swingers. She let me know in a kind way that when I narrowed down what I wanted they could both discuss it but for now I was not what they were looking for.

The other letter went to a woman who was married and swung with her husband and had a boyfriend she also swung with. She had the boyfriend contact me. He told me that they were very experienced swingers and very sexual. She had a girlfriend she swung with as well as him and her husband. Sometimes all together but usually as couples (the wife and one of the other three). This sounded perfect.

There was a catch. The wife had concerns because of my letter that I was very inexperienced and didn't know what I wanted or way too kinky for her. To be clear, my letter listed what I was willing to do and it looked like the list of what a Tasmanian Devil eats.

After a short while it became clear I had not experiences most of the things listed and he politely told me he would be in touch. I thought that would be the end and stopped sending out letters. A while later he called me back. He said they had discussed me. My inexperience was one thing but my interest was another. They felt I was very interested in the kinky and she thought there may be a place for me in their games.

It became clear that they had a narrow focus for their plans for me but it would take in many of my interests. She wanted to make sure I would not be a game player and would actually fulfill their needs. Her boyfriend would be my contact and would audition me to see that I could fulfill my function. It was made clear to me that by the time I met her and her husband I would have to be willing to do what they wanted without hesitation or games.

I never spoke to her only her boyfriend. He wanted to meet me and knowing I was a virgin, he arranged for me to meet a gay friend with him who had experience in sex slavery. He could talk to me and answer questions. At this point I was a virgin and very eager.

Her boyfriend Al met me and we drove to Jim's place. Al was very bisexual and experienced, about 5 years older then me and was into swinging as a single man. Jim was described to me as gay living with a man who was gone for that night and very experienced, kind and knowledgeable.

Al explained that the wife wanted me trained for her husband who was bisexual but she thought preferred men. She wanted this so when she had swinger parties, I would occupy her husband, or when she wanted to go out with her lesbian girlfriend, I would occupy her husband, or when she and Al were together or out, I would occupy her husband. In short, as a present she wanted to give me as a sex slave to her husband to play with.

Al wanted it to be clear, when I met her husband I could not be a virgin. I had to know how to give a blowjob, kiss a man and take his cock up my ass. During our conversation it also became clear that it did not matter if I enjoyed it or wanted it. It only mattered that I did it willingly and with gusto. I could not be shy or inexperienced about these things.

Al thought the wife or some of her girlfriends would also be playing with me sexually as would some of her men friends but I was mainly a gift to her husband. A gift to allow her some freedom to play while he played.

As we arrived, Al told me Jim was very cool and I could ask him anything. When we got in, Jim took us to the bedroom of his apartment which was large with an ensuite. A gay porn was playing as background on the tv. Al asked to use the bathroom after we were introduced.

Jim lay on the bed to watch tv. I had been told to ask anything so I said, "Do you want me to take off all my clothes?" Jim said," Sure." I quickly stripped, looked at him and asked, "Do you want me to get into bed with you?" Jim said, "Sure." Jim got up, took off his clothes and laid beside me. He began to fondle my cock and then we were kissing.

This is when Al returned and said," Wow. That was fast." He stood beside the bed watching us and the movie for a few minutes before he began to take off his clothes and got into bed. He laid beside me while Al went down and began to suck my hard cock, getting harder by the minute.

Jim told me to get up and turn around at the end of the bed. He pushed me forward and had me bend at the waist standing with my hands of the bed. He began to use lube to finger my ass. I was moaning a lot.

Jim continued and was soon pushing slowly into my ass. Al moved himself down on the bed so his cock was in front of my face. He gently pushed the back of my head. My lips opened like a baby bird eating worm. But this was a 9 inch worm that took enormous to me. I had never been this close to a cock before. I began to suck the tip.

I ran my tongue around the crease in the tip. It was different from mine as he was not circumcised. As Al pushed my head down, my lips pushed the skin and I soon felt the head. I licked around it then pushed my mouth further down his cock until I choked. I came up for air and realized my ass was full and Jim had been pushing all the way in. I was now full and he had not been moving.

As my head came up, he slowly pulled back and then pushed in. In and out. While Al said, "Good boy." Al pressed the top of my head back down and I began to suck his cock and grunt at the same time. I grunted with every push and pull inside my ass. I kept doing my best to bob my head and do whatever I was told. No teeth. Slow down. Lick the head. Push down. Lick my balls.

Jim kept two hands on my hips to hold me steady and my forearms were flat on the bed. I had some trouble keeping my balance. This was my audition and I knew I must perform well for my Mistress to pease her. I did it with as much enthusiasm as I could.

It went on forever until I felt hands hold my head and Jim telling me to hold still as he pushed violently in and out of my mouth several times. I felt a warm gush and began to swallow as much as I could. Lots of it sliding out and onto his cock. He was moaning very loudly.

I felt Jim ramming me very fast now and I felt like my ass was on fire as I moaned loudly. I could feel him push all the way in and finish. It felt like he was peeing in my ass with a pulse. He slowly pulled out. I still felt the fire in my hole. I slowly descended to my knees with my face on the end of the bed.

Al and Jim lay at the top of the bed looking down and me and saying I would do. They lit a joint and shared it while I stayed there feeling the cum in my mouth and ass. Jim got up and took me by the hand to the bathroom to wash me and let my rinse my mouth.

Al was enjoying a porno movie when we came back to the room. Jim stopped and suggested we go to the living room. He gave me a very short robe (just below my crotch) with no belt. He had a longer one for himself with a belt. He got us some pop (I told him I don't drink) and we sat on the couch to talk.

We could hear Al moaning in the other room as he was jerking off. Jim said, "That guy is way too sexual. He is also way too loud." Jim asked me about my experience. I told him I have none. He said I got very hard but I had not cum. He suggested when Al finished that I stay behind. Jim felt I should be alone with him so he could relax me and get me off. Jim whispered it was all part of my education now.

As he said this he reached out and pushed aside my robe fondling me and began to kiss me. He pushed his tongue in and I began to respond. It was wonderful. I kissed back, got very hard and we were necking. I was on a couch necking with a man and it was my first time.I felt like the little toy I always wanted to be. This went on until Al came out. He spoke to Jim and left saying he would call me in the morning. He did ask me if it was ok and I said yes.

Jim took me by the hand and led me back to the bedroom and back onto the bed. He kissed me and sucked me for a long time then kissed me again for a long time jerking me. He got up between my legs over me saying he was going to fuck my ass now. I said, "Wait. I know about this." I turned over onto my hands and knees looking back at him.

He was pushed back on his haunches and said, "No. We can do it with you on your back. It will be better this first time." I turned again and lay on my back. He lifted my legs and fingered my ass. After he worked 2 fingers in there, he pushed his cock into me. It will burned a little from earlier. I was waaaay too tight and yelped. We tried several times but I would always say stop.

He did console me that it just needed the head to get all the way in. Once it started it would feel great. It would only hurt for a bit until we got going. I told him okay. He started again. Once he pushed in the sensation of burning and the pain from the pressure lessened. We stayed like that for a bit with him looking into my eyes. He leaned in and kissed my lips then pushed his tongue in and whirled it around.

I kissed him back and he began to pump me. This lasted a long time and when he was ready he pulled out. He told me to hold still and he came on my face, neck and chest. He leaned over, scooped it up with his tongue and fed me his juices. I swallowed everything he fed me.

We lay together holding each other and kissing. He asked me how I liked sucking Al's cock earlier and him fucking me in the ass. I told him I had not enjoyed it. I loved the humiliation of sucking a man's cock for my Mistress who I knew had ordered it. He laughed and said I looked like I loved it. Jim told me that was all that was important for others. If I enjoyed the humiliation, than I got what I needed too.

I dressed and left after kissing at the door. He invited me back but I told him I didn't think it was for me. Jim was clear that the way I kissed back more than proved it was for me. I was good at pleasing men. I told him I hope I hadn't insulted him. He smiled and said, "No insult to me. I know men are going to pass you around a lot. The fact that you don't enjoy it will even things out for your insolence." He made it clear he hoped to see me again and would make sure Al would call him to give me lessons.

The next day Al called and had me come to his house. He was naked when I arrived. He tried to get me to go in the shower with him. I said no. He tried to get me to suck him. I said no. He tried to get me to take a dildo up my ass. I said no. He called the wife about me. She was not convinced I could be of any use to her.

Al handed me the phone. She said I was rebelling this morning and that was not a good sign. I was not to say a word but pass the phone to Al, get on my knees and give him an enthusiastic blowjob. So I did.

As he finished on my face and I was licking cum from my lips and cheeks, he was telling her how great it was. He had given her a blow by blow description. He held the phone to my ear. She was laughing and said, "Lesson 1 was a pass. Your homework this morning was a fail." She instructed me to be ready Friday for Lesson 3. I had to pass Lesson 2 and 3 to meet her for Lesson 4. She hung up.

Al told me to get to the shower to clean up. It turned out the husband was at his office waiting for us. His secretary would let us in so I could spend the afternoon sucking him and being fucked by him. I was not to say anything while I was there. Al told me my loud moaning and grunting was not going to be a problem because the secretary was a friend of the wife and knew why I was going to be there.

I would amuse the husband. He had to be pleased with me. He would tell me what to do and I would without hesitation. I was not to speak or say anything even if he asked any questions. If things went well, Friday I would get Lesson 3.