All the next week, I was nervously awaiting my next meeting with my mystery master. (I'd begun to think of him as a master since I gave myself so willingly to him.) I could barely concentrate on anything that week, other than the great experience I'd had, and what possible things might happen next. His email had told me where to meet him the following Friday evening, as well as what to wear and bring. I was also told that I would not cum or even touch myself at all for the duration of the week.
Friday came, and I put on a cock ring, jock strap, baggy mesh shorts, and no shirt, as the email had said. I felt somewhat self conscious about showing off my chest and abs for anyone who might see, especially when I was needing a shirt to conceal the raging hardon in my jock strap. But I could do nothing, I wasn't even supposed to adjust myself, although I'd done so throughout the week, I figured he wouldn't know. As the meeting neared, however, I took his instructions more seriously.
I walked back to the hotel, I guess he wasn't into much variety, and walked up to the room. From the outside, I could tell this room was bigger, he must be wanting more extravagance as time goes on. I walked in, as instructed, and stood at the door. He had said in his email that he would come to me when he was ready. I waited for endless minutes before I heard footsteps coming. As a figure entered the room, I became mortified. Here I was in basically just shorts, which were quite tented, and I see my biggest crush from high school. Clearly this wasn't the right room to be in, so I turned to walk out. He quickly walked over to me, and pushed me back onto the bed.
Stuttering, I asked, "what are you doing here?"
"I had so much fun last week, I figured it'd be fun to come back and abuse you some more." It suddenly hit me that he must have been the one who came back in while I was duct taped to the table. The laugh had been a different person! He laughed as he saw my realization, and that sound only served to prove my theory.
I still couldn't believe that I had submitted to this person I had lusted over for so long. And for him to have seen me naked and tied down, it was so embarrassing! As I lay there stunned, he began gathering his equipment for the evening's events.
"Did you have fun last week?" I heard him ask.
My response was a long time coming. "Um, yeah, I guess....I just didn't think it was... with someone I knew"
"Well believe it, and it's gonna happen again. I think we've stumbled across something that works well for both of us, you're willing to take pain and humiliation, and I'm more than willing to give it." Receiving no response from me, he continued, "This could become a very frequent occurrence, it'd be great to have someone like you around. Too bad you didn't ever let me know you were this way back in high school. Now take off those shorts."
With only a little hesitation, I complied. It just felt right to be doing what he was saying. "You haven't jacked off this week, have you?" he asked.
"No, of course I haven't."
"That's good. Get used to it being like that. Now come over here and bend over."
I hesitated again, it was just so much different knowing that I was being humiliated by someone I knew. How could I bend over right in front of someone I'd lusted after? I decided there wasn't much choice, so once again I complied with his order.
"You're gonna have to work on moving faster than that, otherwise I'll have to teach you to." Saying that, I felt his hands push the now-familiar butt plug in. My cock pulsed at the slightest contact with him. "You really do like that when I touch you, don't you?" he asked as he stroked the pouch of the jock strap. All I could do was moan in response, I was still too stunned by the fact that this hot guy was doing this with me, touching me.
He slapped my ass and slipped the collar around my neck again, grabbing it to drag me into the bathroom. "You're gonna clean yourself out now, cuz I don't do stuff like that." I saw the enema bag and realized what he meant. I walked over, filled up the bag, and proceeded to "clean myself out." As I did this, he walked back out into the bedroom. I heard him moving around, but didn't think it would be wise to walk out and see what was going on.
After I seemed sufficiently clean, I tidied up the bathroom and sat on the toilet, waiting for what would come next. After a couple minutes of anxious waiting, he came in. "Drink this," he said, "it'll make you less nervous and uptight." I took a sip and realized the high alcohol content of what he'd handed me, but figured it probably would do me some good to be a little looser for the rest of the night.
I finished the rest of the drink, and was feeling pretty good. He grabbed my collar and dragged me, willingly, into the bedroom. He dragged me to the middle of the room, then stopped. He kneeled down and grabbed something from under the bed, saying "Now it's time to see just how tough you are." He slowly and seductively removed my jock strap as I tried to rub against his hands. Wrong move.
"Don't ever do that, you'll get off when I want you to," he said. An instant later, he slapped my balls and I doubled over in pain. I'd always gone to great lengths to ever keep that pain from happening, and one attempt at pleasure had brought it upon me.
He lifted me back to a standing position, tied some string around the base of my scrotum, and cut the string so that it hung at about knee level. I saw him grabbing for something else, and watched as he tied it on the end of the string. The thing must have weighed at least five pounds, and it hung near the middle of my thighs, pulling down my balls pretty good.
"This is a three pound weight, we'll start with this and see how you handle it. Since it's your first night with this, I might go easy and take it off if it gets to be too much. I also want to get you started servicing me, that's part of every good little slave's job."
Fear overtook me as he said that word. "Slave," I hadn't thought about completely giving myself to him, but then again, I'd be stupid not to want to be with this guy who turned me on both with his looks and intelligence. Still, that was a big commitment, what would happen if I did become basically just his property?
I figured I'd speak my mind, "Um, I'm not sure I want to have a slave/master type thing, that's a lot of commitment and I've just barely experienced anything close to that."
"Alright," he said, "we'll keep meeting on the weekends, and see what happens. I will introduce sexual services into this, though, it's been too long since I've had any action, and besides, I can tell you want it." That was mostly true, I would do almost anything to be able to see him naked, touch his body, taste him. And it's not like my raging hardon wasn't giving me away anyway.
"Now what do you think we should do first?"
"Well," I said, "I kind of liked the bengay on my cock and balls, maybe you could do that." Truth was it wasn't the greatest feeling, but I figured it'd be better than what he might come up with.
"Don't worry, we'll get to that soon enough. But I have something else in mind for now. Raise up your arms, and spread out your legs." With that, he proceeded to tie me basically spread eagle, but standing up. My arms and legs were tied out to my sides so that I couldn't move them. It was basically like how I was on the bed the week before, but he had access to every part of my body.
First came the clothespins, on my nipples, armpits, abdomen, cock, and already hurting scrotum. Even with the alcohol in me, I was definitely feeling the torture he was putting me through. I'd been curious before and tied weights to my balls, but there was always the option of untying the rope and relaxing. I didn't have that luxury this time, and it hadn't sounded like I'd be relieved of the weight any time soon.
"You know, I like you having a smooth body, not that I saw you before you were shaved. It makes you look like a little boy, it's hilarious. You'd better get used to it staying this way."
"Yes sir." I didn't realize my slip-up until after I'd said it, but it just sounded like the thing to say.
"That's what I like to hear, you can and will only call me sir from now on." What had I gotten myself into, first I'm tied up and giving my body to him for his pleasure, and now I have to call him sir? I didn't know if I was ready to be starting something like that, but it was too late.
He walked around me, looking at either his job, or my body, I couldn't tell which. I knew where I was looking when he was in front of me, though, right at his pants, trying to imagine what it would look like if they were gone. That was not to happen for quite a while, however.
He proceeded to put almost 50 clothespins all over my arms, chest, abdomen, cock, thighs, and balls. It was beginning to seem like he had an almost endless supply. Finally he stopped and stood back to admire his work. He seemed pleased, and I could only wish I was able to see what I looked like. He disappeared behind me and I felt his hands between my ass cheeks. He was pulling out the butt plug, only to replace it with a vibrator. "Let's see how long you last with this in. If you come before I decide to turn it off, you'll regret it." With that, he turned it on.
I had no idea how I was supposed to survive indefinitely with this thing in, I had no control whatsoever. Whenever I jacked off, I had done it as fast as possible to feel that great feeling, I didn't know I should have been preparing for a day like this! 'Please let him turn it off quick,' I thought.
I felt my orgasm coming as I tried all I could think of to stop it. I was terrified at what would happen if I were to shoot. I knew whatever it was, it would most likely be painful. Just before I reached the point of no return, the vibrating stopped.
"Dammit, the fucking batteries must have died. You got of lucky this time, buddy. Oh well, I guess we'll just have to move on," he said. I was glad I was going to be rid of that big thing sticking up my ass, it really wasn't too comfortable in this position. But all I felt was a strip of duct tape being applied in my ass crack over the vibrator. "To keep it in," he answered my unasked question.
"Since it's getting late, I'll do one more thing, and then we can get some sleep." That was just what I wanted to hear, I didn't know how much longer I could stay there tied up. He took off all the clothespins and then I felt his hand on my cock and wondered what was going on. Was this another test, was I supposed to hold out again? Again, he answered, "You have a minute to cum, or it's not going to happen for a long time." Normally, a minute would have been more than enough for me, but with the pain, it was going to be close. After almost a minute, I shot, and realized he'd caught it in his hand.
"We're not going to be wasting any of this, so it's going to be your job to eat whatever gets shot out." He put his hand in front of my mouth, and hesitantly I licked. After a minute, I had cleaned all my cum off of his hand, and he was satisfied. "Hope you enjoyed that a lot, because it won't happen often," he said as he began to untie me.
As he was untying me, he suddenly stopped and said, "Oh yeah, I almost forgot you had wanted some bengay, don't want to disappoint you." I mentally kicked myself, the night could have been over if I hadn't mentioned that. I got some out and slathered it on my cock and balls. Then he ripped the duct tape off my ass, put some up and down my ass crack, and reapplied some duct tape. "Now we're done," he said as he finished untying me. "Take off the cock ring and the rope around your balls, put on your jock strap, and get to sleep."
I headed for the bed as he yanked me back by my collar. "See this?" he said, shaking it, "This means you're no better than a dog, and dogs sleep on the floor. The bed is mine. Now get to sleep."
"Yes sir," I relented.
Much welcome sleep came soon, but it wasn't going to last long enough.