I was laying on Paul's bed in a jock with a plug in my ass when the man came in. It was nearing December and winter was hitting hard. The man took a while at the door, knocking his boots off and then taking off all his winter gear. He was late for this and both Paul and I had been sitting around waiting for him to come. As he stood in the door he gave Paul some excuse about having trouble getting off from work early. Then I heard him ask, "Where is it?"
He and Paul both walked to the doorway and looked at me on the bed. Paul had told me to keep playing with myself while we waited so that I was hard in the jock when he got there. The plug in my ass had helped by keeping a constant pressure on my prostate. Apparently I had done well, because the effect of my body spread out on the bed was clear on the man's face. His eyes lit up and he quickly started to take all his clothes off.
"I take it you like?" Paul said, holding out his hand.
The man fished in his pocket and pulled out some bills, quickly handing them to Paul. "Yes. It's perfect. You always know what I want."
Before the man had arrived, Paul had told me everything that was going to happen as he worked my ass open with his fingers and then the plug. "Some men, especially older men, like to pay for sex. I don't expect you to understand that. It is just a truth."
"I get it," I replied, even though I didn't. In a way I still don't.
"If you do well today, I may let you do this in the future," he told me. I was fourteen and new, so I didn't really get that I could do this on my own. I didn't need Paul to pimp me. But the idea of Paul getting more men to pay to fuck me was really hot. I promised to be on my best behavior.
I almost fucked it up, though, while the man was undressing. He stripped down to just a baggy pair of long-johns that didn't seem to fit him and also had a wide hole on the upper thigh. He looked kind of silly standing there with lust in his eyes, messy hat hair, and a hard cock in his ratty long-johns. It was like looking at a man who had just emerged from the woods after a few years. I had to struggle to suppress the laughter that was a combination of my nerves and the strange looking man that was standing over me. I got a look from Paul that told me to keep it cool, and I did. I swallowed and managed a smile that I hoped was inviting, and not mocking.
I can only imagine what must have been going through that man's mind when he looked at me. I was fourteen years old, but with my already ample body hair shaved off for swimming, I looked much younger. I was tall, but had been the same height for a few years at that point, still wearing clothes I had bought in sixth grade. I was spread out on the bed in nothing but a jock strap, smiling. I must have looked very young, but not nearly as innocent as I should have.
The man crawled up on the bed and while Paul supervised from the door he pulled my jock down. My teen cock sprang up in front of his face. He licked his lips and then slupred my cock down to the base in one quick motion. I arched my back on the bed at the unexpected-but-pleasurable feeling his mouth created. His hand moved down past my balls and felt the base of the plug sticking out of my hole. He moaned in appreciation around my cock and lifted off. He turned to Paul and said, "You plugged it up? Nice."
"It's a pretty big plug, too. You should take it out and see what that hole can handle."
Despite the big compliment Paul had just given me, I found myself growing annoyed that the way the man referred to me as "it." It was like a little thing in the back of my head twitched every time he did it. But I knew that I really was just a sex object to this man. After all, he had paid for me to be here. I resolved myself to not let his objectification bother me: a big step forward in the self-confidence I had been gaining since the previous summer. The twelve, even thirteen year old me would have let his use of the word "it" bug me until I wanted to run away. But recently I had been developing a "why should I care what people say" attitude that I let take over my mind in that moment. Why should I care that he won't treat me like a person? He's paying me to do something I love. I'm still on top.
Years later I would read those words in my journal while preparing to write this post and think, You go.
The man pulled the plug out of my ass slowly, almost shaking with excitement as he saw what came out. It wasn't a huge butt plug, by any means. But I had been slowly working up from the smaller plugs, loving the full feeling I got from having a large object stuck up my ass. The moment the plug was out his fingers were in and He was pushing my legs back to get at my hole. I grunted a bit at the entry when he began fucking, but the half hour or so of being plugged had made me ready for him, which was good because he started rapidly fucking and didn't stop until a short time later when he shot his load in me.
He pulled out, still wearing those ratty long johns, and moved down off the bed. He looked over at Paul and started to babble about the great time he had had fucking me. I stayed where I was while Paul helped him find all his clothes and walked him to the door. Paul came back into the room and, as usual after he had shared me with another man, fucked me too, jerking a load of cum out of me before he shot in me. He was gentle and loving, kissing me all over, paying a lot of attention to me. I easily picked out the difference between what Paul and I were doing and what that man and I had done, and I suspect Paul had wanted me to.
When he was finished he plugged my ass again and had me do some homework in the kitchen before I left for home. Right as I was going out the door he stopped me and said, "Don't forget this," as he placed the money in my hand. It was almost a shock to me, having that much money suddenly mine to spend. "You did a great job today," Paul told me, "And if you keep doing well, you'll get more money." I remember him putting his hand on my shoulder and saying in a very serious voice, "You can't tell anyone where you got that money or how. Don't spend it all at once and don't let anyone know. Do you understand?" I nodded, excited but also very aware of the implications of what I had just done.
It was the first time I would get paid for sex and it wouldn't be the last. It was never a regular thing with Paul. The group of close friends that regularly played with me and went to his parties rarely paid for my services unless I performed exceedingly well. The money was just every so often. But it was enough to pad my bank account and to buy the books and clothes I wanted. My parents never checked my bank statements, expecting me to be an adult about my money, so I never got caught.
I also never got into trouble as long as Paul was acting as my pimp. It was years later when I turned to others that some trouble started. But that's a story for another post. I don't regret or feel ashamed that I was a whore. In fact, I've gotten paid for sex within the past six months. I don't feel angry or hurt about any of it, though I must add that I certainly don't support the use of underage teens as whores. As far as my feelings on legalizing prostitution for consenting adults: I think it is great. Just shooting out a disclaimer so I don't get too many flamer comments.