Friday A little background info: Jason and I had been dating for about a month. He was a year older than me and my parents thought we were simply good friends.
A year or so before that, I had made the realization that I find men just as attractive (sometimes even more so) than girls. I had had a few girlfriends before, nothing lengthy, and none were terribly deep either. The routine was the same each time.
Get a huge crush on them, become friends with them, eventually as them out, get to first base (making out in my opinion), get tired of that, unsure of how to go further, do something stupid and break up. It generally took about three months. We had met online in a chat-room.
I had been surprised to find someone so close to my area. Most of the time I just chatted up bondage with them for a while before getting bored and blocking them. He was different somehow; he knew what he was talking about with regards to the BDSM lifestyle, yet wasn't one of the more hardcore practicers. Finally we got together and started dating. Things started slowly, to both my disappointment, and my elation. It was different than my past relationships, I had met someone I actually liked spending a lot of time with and had things in common with.
We hadn't even done anything sexual or bondage related for that month, hence my slight disappointment, however things were about to change. I was at Jason's apartment one Friday when he issued a challenge. We would lie naked next to each other side by side, and simultaneously jerk each other off. The person who came first would be the loser and have to be the winner's slave for that weekend. Jason was the more dominant of the two of us and was able to convince me to be on his right side, essentially forcing me to use my left hand on him.
Awkwardly, but determined, I treated him like myself, starting off running just my thumb and index and middle finger slowly up and down his seven inch circumcised cock. Either I wasn't doing very well, or he had excellent control over his body because I had barely gotten him hard, and I was already starting to feel the barely palpable touch of my orgasm. Knowing I was far behind I tightened my grip and started working him harder and faster.
It worked, but only slightly, his dick reached its full hardness, but his breathing remained steady, whereas mine was quickly becoming short, ragged gasps. It now took sizeable concentration to keep myself from cumming, something that took away from my handjob. Suddenly, a strong forced orgasm and gushes of cum escaped my dick squirting all over my stomach and up to my chest.
Grabbing some tissues from the side of the bed he wiped me clean and left the room.
He returned with handcuffs and an armful of rope. "On your stomach, hands behind your back," he ordered. Remembering my promise I complied, my cock already starting to grow again against the mattress.
Quickly and skillfully he bound my wrist together tightly. "Is that too tight?" he asked. "No," I replied, only to be met with a sharp swat on my ass.
"No, what?" "No master," I corrected myself. "Much better, slave," he replied, "now spread your legs." I did as he told me, and soon felt a metal buttplug being shoved into my ass. The width of the top caused me a small amount of pain as he inserted it, but once it was in, that same width kept itself there.
"Now, get on the floor, onto your knees and finish what you started slave," he said holding out his cock. As quickly as I could, I scrambled off the bed and onto the floor, the fact that my six inch cock was now fully erect again was irrelevant, it would be time for him to get pleasure. Before I could begin he grabbed my head and locked a collar tight around my neck with a D-ring at the front. "For every five minutes that passes that I don't cum, you're going to be punished," he said looking at his watch.
I began licking his balls, taking one, and then both into my mouth, I massaged them with my tongue. Slowly pushing them out of my lips, I then licked from his balls all the way up and off the tip of his dick, finally bringing my lips to rest wrapped around his cock just past the head. I began exploring him with my tongue rubbing it lightly over and over the tip, then circling slowly down around his head.
I got down farther than I thought I would, a good three inches before I became all too aware of his dick in my throat. Continuing to lick, and keeping my lips wrapped tight, I bobbed up and down.
It took a while for the soft touch of my lips and tongue to do anything, but after a while he began to moan and thrust into me each time I went down. He was getting another inch into me and I still wasn't gagging, a good sign.
His dick was now soaked with my spit as I moved up and down faster and faster, getting him closer and closer to orgasm. Finally he took over letting me wrap my lips around the very tip as he jerked himself into my mouth. His cum shot a few streams then oozed out over my tongue as I got him off for the first time. He tasted excellent, the bitter and saltiness that I expected barely noticeable.
I read somewhere that a diet full of fruit caused ejaculate to taste better and thought back to the pineapple that Jason so thoroughly enjoyed. When he was done, Jason slowly slid his wet member out.
"Very good, slave," he said affectionately.
"But that took far too long. Your first punishment is that the plug stays in." I felt for the first time in a while the buttplug that was currently graciously filling the confines of my ass. Not too bad if I stayed still, the inch thick piece of equipment became very noticeable when I moved around. "Secondly, you're going to wear this," he strapped a ball gag around my head. The large red ball forced my mouth wide open around it.
"Also, you'll wear this," he fastened a cock-leash to my hard dick. "You will refer to me as, 'Master,' or face the consequences." I nodded with agreement. He led me out of the bedroom into the living room and stood me by the couch, off to the side so he could watch TV.
He had with him a single tail whip. During commercials he took great delight in whipping me until the program was back on. He seemed to want to focus on my exposed belly, giving me stripe after red stripe. Every once in a while he attacked my thighs and what parts of my ass that weren't covered by my bound hands.
Slowly his torture of me began to get him hard again, my soft grunts through the gag and my minute twitches pleasing him. After a while he got two clothespins and put one on each nipple. Then he amused himself by trying to whip them off. There were several new red stripes on my chest before the second finally fell to the ground with a clatter. Satisfied, and now fully hard, he got up, removed my gag and pushed me to my knees.
I took his barely dry cock in my mouth again. I tried to see how far I could take him. I got four and a half inches before his cock in my throat forced me to stop.
Concentrating, I pulled off, took a moment to try and relax myself and tried again.
I got a full five inches before I panicked and had to pull up. Jason realized what I was doing and encouraged me. "You can do it slave, take your time and relax." I slid my lips down him again, this time reaching success, getting his whole cock in my mouth and down my throat, but again I panicked and was forced to pull up quickly.
This happened three or four more times before I was finally able to hold myself down for any measure of time. I continued to work at killing my gag reflex while I serviced him. It took another half hour of work before I could hold myself all the way down for an indefinite period of time.
Jason said I was lucky, it wasn't usually that easy. I finished him off that way, sliding all the way down and all the way up making sure my tongue washed graciously over the right spots. Like before he jerked himself right onto my tongue allowing me to enjoy every drop of taste from him. With my newfound skills, he decided I should hold myself all the way down until his hard-on went away.
I complied dutifully as it was only a few minutes later that his fully flaccid cock slid out of my mouth. When he was done, he untied me and walked into the kitchen. Opening a draw he pulled out two things and handed them to me; they were a stud finder and a 2 inch diameter eye-screw.
"Put this in the ceiling where you were standing earlier so I can bind your hands above your head." He went into the bedroom for something. I grabbed a chair and looked for a place to screw in the new tie-point. I found the beam a few inches off of where I was and began to put it in.
It was hard work upside down through the tough ceiling, but eventually I got the thing all the way in.
I put the tool back in the kitchen drawer and waited. After a bit he came back out and eyed my work. "Very nice," he smiled, kissing me and giving my hard cock a few good rubs. He then proceeded to tie my hands together in front of me.
Raising them above my head he stood on the chair I'd used and Tightened the rope until I was almost forced to stand on my tiptoes. "There, now you're very, very vulnerable," he said with a grin. To my dismay he pulled the forgotten buttplug out of my ass, tossed the condom into the trash and placed it aside. He started whipping me again, all across my fully exposed stretched belly.
More red lines appeared as he kept at it, harder and harder until I started to whimper. After I started to all out yell each time he lashed my skin, he paused. "Beg for it." "Please stop master." A sharp lash across my waist.
"I beg you, please stop whipping me, I'll do anything." That got his attention. "Anything? Like what?" "I'll be your slave for good." It was the first thing in my head and the first thing out of my mouth. "Really?" I nodded, "yes master." "You'll have to prove it to me, pass certain…tests." "Yes master." "Alright, for now you are still my temporary slave." He let me down and untied my hands.
"For your first test, I want you to go down to the street and stand there until I say you can come in. Naked." "Yes master." I walked out the door, down the stairs and out the door of the building. The doorman gave a curious look, but said nothing. I stood there staring up at his second story window for what seemed like hours.
It was late so there were very few people out, and no one drove by. Finally he said I could come in, but to take the elevator. I found him in it.
I was to service him while it made the short journey to the second floor.
I did so without hesitation, sucking his cock through the slit in his boxers, exercising my new deepthroating skills. A minute later the doors opened to reveal a somewhat surprised man in his 40's. Jason zipped himself up and led me back to his apartment. Once inside my collar was flipped around, and my arms bound, raised then bent behind my head and tied to the D-ring. I was allowed to finish my blowjob. I took my time going all the way down and back up. Letting his balls slap my chin, and rubbing his tip over my lips.
I got him horny very fast. This time he let me take him all the way myself, cumming all over my tongue again. Some trickled down my chin and he helped me clean it up by wiping it off with his dick and having me lick it clean. I was to go to bed bound this way so he would have unhindered access to my body at all times. We spooned together, him in back, his hands roaming freely, and waited for tomorrow.