Leather Skin Biker

There is this boy who lives in Indiana who I will refer to as “hotelbear.” He’s a good kid, and wants to be a master one day. He’s about 30 y.o., stands around 5 foot 10 inches tall, with brown hair, green eyes, and a hairy body. He’s fond of the baseball cap, big T-shirt look. As a matter of fact, I’ve never met him, but I feel I know him fairly well. This guy looked to me for mentoring on becoming a master. He was full of questions about how to find a slave, now to train the slave, what does it take to be a master, etc., etc. I kind of took him under my wing for a while, and tried to help him find himself. He had doubts about his ability to be a master, wasn’t sure of himself, and that kind of thing. In the course of our many chats, we spoke of my slave more than one time. hotelbear took a liking to my slave, and wanted to know all about him, how I found him, how he came to live here in Chicago with me, etc. After quite some time, probably six months or so, I felt fairly comfortable making arrangements for my slave to visit and serve hotelbear. This is a post detailing how I pimped my slave out to hotelbear.

What? Pimp my slave out, you ask? Yes. It was part of the headspace. I got off on it, my slave got off on it, and so did hotelbear. It was a win-win-win situation. hotelbear would get the opportunity to meet and play with my slave, and my slave would get something he wanted. On more than one occasion my slave has asked me whether I would be willing to let him try working as a rent boy, or at the very least a male escort. As tempting as that might sound financially, I have never felt that it would represent a good life for him, and could be frought with dangers. Since one of my primary jobs is to protect my slave, why would I knowingly put him in harm’s way for financial gain? That’s not to say that it does not appeal to me on some level. My slave has modeled in the past, and I think I could earn good money pimping his ass out. I’ve checked out what some rent boys charge and found that some command up to $2,000 for a full night, or $200-$500 for an hour. I have a friend who has a friend in the business, so I could ask him for the inside scoop if I were to pursue something like that.

But the hotelbear scene was not a bona fide rentboy situation. I wanted to share my slave with hotelbear, and close to the day of, I threw out this idea for him to send back some green with my boy as compensation. hotelbear said he was down with that. It turned hotelbear on, it turned me on, and it turned my slave on. I once had a guy tell me before I went over to his house to play that he was going to put a $20 on the dresser for me to take when we were done. I have to admit that it was a huge turn on for me, and apparently did something for him too. And when I spent that money, I really, really enjoyed spending it. It was like the easiest $20 I ever made in my life. Basically all I had to do was let him suck me and piss all over him. That scene worked for me on a lot of levels.

So the thing about hotelbear is that he lived in Indiana at the time, and it meant that either my boy could drive all the way down there, or I could put him on the Metra South Shore Electric Line commuter train, and hotelbear could pick him up at the station. And then from the station it was about a 30 minute drive south. The other thing about this situation was that I let my slave stay overnight, in another state, with no car. Those were considerations, but as I mentioned previously, I felt very comfortable with hotelbear. My gut told me that he would be 100% respectful of me and my property.

My slave got ready, packed a little bag and everything. I felt kind of sad to watch that, and to take him to the Roosevelt Road Metra train station. But he was going to have fun, it was a gesture of goodwill toward hotelbear, and he would come back with a little something that he, errrr, W/we enjoy, especially him. I had discussed with both my slave and with hotelbear what my hard limits were for the visit. Namely, no drug heavier than weed, no barebacking, no permanent marks, no blood, scat, women, or animals. hotelbear was willing to comply with those limits. Obviously, it was fine for hotelbear to get my slave high on weed, fuck him, piss on him, and so on. hotelbear didn’t have a lot of his own gear, so he borrowed some from a friend of his. hotelbear is different than a lot of the doms who have asked to use my slave in that he’s not very experienced, and not particularly confident either. But he is definitely earnest, and wants so badly to become a master and slave owner. I felt the experience would be beneficial for him.

I walked with my slave up to the train station. There was no ticket agent on duty, so he had to pay for the ticket on the train. I gave him enough money to travel round trip, plus an extra $20 for incidentals. he had his debit card on him as well, so he could buy his own food and such. I didn’t ask hotelbear to buy food for my property. Feeding him is my responsibility. Feeding, clothing, nurturing, protecting, mentoring, educating all fall into the category of my responsibility. I kissed my slave goodbye and watched him select a seat on the train. And then, within a few seconds, the train pulled away. I have a real hard time with goodbyes. I hate to say goodbye to people when I know it is going to be for an extended period of time, or if they are going “far” away for a while. I felt a little sad watching him go, even though it was just for an overnight in an adjoining state. I was worried that he’d miss his stop and end up riding the train all the way to Michigan City or something. I told him to stay awake and pay close attention to the announcements so as not to miss his stop.

hotelbear would be waiting in his car at the train station. My slave was to find the car in the parking lot and just hop in. The plan was for hotelbear to hood my slave for the drive from the train station to his house. So I understand that hotelbear did hood him for the drive, not removing the hood until my boy was inside hotelbear’s house. hotelbear had offered to let me watch some of the action via Web cam, but I had decided to take a pass on that. I wasn’t there with hotelbear and my slave to see everything that went on, but I do know that hotelbear got him high, that he sucked my slave’s dick (hotelbear loves my slave’s dick and his cum), pissed on him, and fucked him wrapped more than one time. I also heard that a fair amount of time was spent just hanging out, eating, watching TV, etc. I remembered thinking at the time that it seemed odd for a master wannabe to suck a slave’s cock, but that was before I became more enlightened about a dom/master/Sir type having the prerogative to do whatever he likes, regardless what some casual observer might think of it. Using my newer logic, I could say that my boy was serving hotelbear when hotelbear sucked him off.

I believe in never saying never, but I, personally, have not yet chosen to have my slave serve me by sucking his cock. It’s one thing for a master to command his slave to fuck him. That already I can wrap my brain around, as you may have recently read in my “Labor Day Epiphany” post. But me sucking my slave’s cock? I’m sorry, but I just can’t find it within myself to see how that isn’t submissive. What I’m saying is that cocksucking, by its very nature, feels decidedly more submissive than getting fucked. I understand that a cocksucker has a lot of control over the situation, and in a very real sense has power, because of the vulnerable position of the suckee—after all, his penis is surrounded by (hopefully) 32 teeth that could do major damage.

In that sense, the cocksucker has a huge amount of power and control. But putting that consideration aside for a moment, I still say that a cocksucker is a sub bitch boy when he sucks a cock. I don’t say that in a demeaning way at all. In fact, I think that cocksucking is one of the most mutually rewarding acts possible between two men, and that there is a real beauty in it that I find highly gratifying. And at the climax of the act (and the man), the man doing the sucking gets a reward, a gift. He receives the most precious gift that a man can give: the gift of his seed, sperm, spooge, spunk, cum, load, swimmers. That gift is the essence of the man, an extension of himself that a cocksucker can take away with him and keep. Is there a more masculine, more intimate gift one man can give to another? I’m hard-pressed to think of one. Maybe that’s the key to me being able to see sucking cock as a dominant act befitting a master, but I’m just not there yet. But I digress, a lot.

That night, while my slave was down at hotelbear’s house, I thought about him and missed him a lot. I considered him to be safe, so it was not so much safety that was a concern. I suppose it was just more not having him about the house that bothered me. The place seemed empty without him. I can count on my fingers the number of nights that me and my slave have been apart since his first trip back home in December 2005. It’s very rare that we spend a night apart, so the night with hotelbear was kind of a big deal. But the time passed quickly, and hotelbear agreed to put him on a late morning train, so my boy would be home before lunchtime next day.

The next day, my slave arrived right on time. He called me about five minutes before his train pulled into the station, where I was waiting. He stepped off the train, took one look at me, and the first thing he said was “I missed you so much, Master.” I told him I missed him too. I text messaged hotelbear to let him know that my slave arrived safely. As we walked home from the train station, my boy told me all about his adventure serving hotelbear, and he reminded me more than once how glad he was to be home. When we got home the first thing my slave wanted to do was shower. Before he got in the shower, he went to the bag he’d carried on the trip and pulled out a small ziploc bag containing the green hotelbear had promised in return for use of my boy. So there it was—compensation for services rendered. I’d pimped out my boy and the proceeds were finally in my hand. Hot.

This entry was posted on Thursday, June 12th, 2008 at 7:04 am and is filed under Cum, Dominance, External, Fucking, Pimping, Sir/boy, Submission, Sucking, Swallowing, Watersports, Wrapped.