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Dating on line
I had never tried on line dating, and had no need to, since, and it is hard to say this without sounding like I am bragging, but I am reasonably good looking, 20, bi, blonde, 6', 185 lb, athletic, blue eyes, 7" cut, and have never had an issue attracting guys (and girls).
But it was fall break, the campus was almost empty, at least my dorm was, it was raining cats and dogs, and so "The Playground" (the nearby city cemetery where one could hook up in good weather) was out, the gym and the library were closed to insure that all the students "took a break", and I was horny.
So, I went on line to see what I might find. Now Philadelphia is a big city, and there were hundreds of guys available. I conversed with a few, tried to eliminate the nuts and the photo seekers, and narrowed it down to a professor who taught at another Philadelphia college, and who taught drama, something I was very unlikely to ever take a course in, so we would not have an issue about that. They were also on fall break. I got an Uber, my truck was parked in a garage a mile away where I kept it since there was no student parking on campus, and went to his place.
Jackson was about 45, lean, totally gay, as he told me, had never fucked a woman although he had tried a few times, a bottom boi, and into mild S & M. All of that was on his profile. He was 5' 6", 140 lbs., greying hair, kind of a Hollywood good looking. He was wearing a fancy dressing gown, like in the movies of the 30's and 40's, maybe it was a "smoking jacket", but in any event he had that, and loose silk pajamas under it, and slippers that looked Chinese.
We talked a bit, he had tried being an actor in Hollywood, and had bit parts in a few movies, none of which I had ever seen, and with a college degree found teaching a far more reliable way to earn a living, and appeared a few times a year in college and local amateur productions.
"Have you done any S & M?", he asked.
"No, but I am interested in what it is all about, I have seen it on the web."
"Are you new to gay sex?"
"Not really, I have been playing all along, but, most of it has been pretty vanilla. I have done a 4 way and a 3 way, and a bi couple, oral and anal, and of course hand jobs, some toys, pissing once, but never any S & M, and since so many appear to enjoy it, when I saw your profile, I thought this might be a good chance and given that you are a teacher, you might be good at teaching me."
"Right on," he said, "come this way to my bedroom." I did. The walls were painted a dark red, the drapes were black and drawn over the window. The bed had a black bottom sheet and red pillow cases on 4 pillows, but no top sheet or blankets. Hanging on pegs on one of the walls were a variety of leather straps and other contraptions, dildos, what I was to learn were cock cages, butt plugs, a few whips, chains, handcuffs, both "regular" and padded, ankle bracelets, and other things about which I had no idea.
"Do you know about safe words?" he asked.
"Yes," I responded.
"How about "ghost" as our safe word, after all, it is almost Halloween?"
"Ok by me."
"If either of us say it, we both stop, and if it is repeated, we back up a step, or two, from whatever we were doing, and reset."
"Ok."
"Now, let me see that athletic body of yours." We both stripped. His body was toned, not overly muscular, but very nice. His cock was bunched up in a cage like thing, with a leather strap around the back of his balls. His nipples were pierced with bars with balls on the ends, and his cock appeared to be fitted with a PA. He also had a bar through the front of his ball sac.
"Very nice," he said to me. "Do you like what you see?"
"Yes, but I am curious about what I see. Tell me about the cage on you cock."
"That is so I can't play with it. It is a form of mild torture. It is trying to get hard, but can't, and I can't really stimulate it, it hurts a little, but not much. The key is in the butter compartment of the refrigerator if you need to get it to release me, but that is just in case. You probably will have no need for it."
"And, the nipple bars?"
"It makes it easier for you to pull on my nipples, and make them hurt, if the hurt is too much I have the safe word. `Ghost'."
"Didn't it hurt to have them put in?"
"Yes, but I get pleasure from the pain."
"And, the bar through the ball sac?"
"It really just goes through the skin and not into the space, but that hurt as well."
"And, is that a PA?"
"Yes and that hurt the most. It was really painful, and I could have had an anesthetic on it, but I was tough and made it. I had a doc do it, he is gay, and is the go-to MD for us guys who want a doc we cannot shock and who won't be judgmental."
And with that he lay down on the bed sideways, with his head hanging over the edge, and said, "Fuck my mouth, and do it now." So, I did. It slipped right down his throat on the 3rd push, I could see the outline of it on his neck. He put his hands on my ass and guided my moves. His cock was red and straining against the cage, all bunched up inside it. After a few minutes of this, I was ready to cum, and told him so. He asked me to then pull on his nipple bars, gently at first, then harder, and then even harder, and then to pull on his balls with one hand. He had big balls, not as big a mine, but big and they pulled down a good ways. So, my cock and both hands were busy.
He pulled away, and said, "Now, let's try something else, were you turned on by that?"
"Yes, I almost came."
He got up and went over to the stuff on the wall and got a leather harness with straps that crossed in the front and the back, over the shoulders, and around his waist. It crossed his nipples and had little slits to put the nipple bars into. "Now, I want you to fuck me, doggie, and pull on the harness, and tell me what a good boy I am, to begin with, and if you can hold out, keep it up and switch to telling me what a bad boy I am, and pull harder on the harness as you fuck me harder. Can you do that?"
"I'll sure try," I replied. And I did. Condom and lube, his hole was prelubed, I sunk right in, and started fucking him, slowly. "Good boy," I said, "good boy, take my big cock, and make me feel good." Then he started to try to get my cock out of him, and it was time to switch, to "Bad boy, bad boy, I need to teach you a lesson," and I fucked harder and pulled on the harness harder until I was holding his whole upper body weight with the harness. My balls were slapping against his taint, he was moaning, "I'll behave, I'll behave, stop, stop, you are hurting me," and I just kept on fucking, harder if it were possible.
"Ghost," he yelled, and I relaxed my hold on the harness, letting him down on the bed, but left my cock in. "Ok," he said, "enough for now, pull out carefully, and we will think about doing something else." I did.
He turned over and lay back on the bed. My cock was so hard, it was standing up and throbbing. His cock was bright red, and covered with cum, bunched up inside the cage. He took off the harness, his nipples were bright red and looked kind of bruised, which they were. "You did good," he said. "I came inside the cage."
"I can see that," I replied.
"It does not always happen, can you go to the refrigerator and get the key out of the butter compartment? And get the can of whipped cream as well?
While I was doing that he placed a few towels on the bed. "Please unlock the cage, if you can."
I did. His cock flopped out, all wet and sticky, and half hard. "Do you want to lick it off, and transfer my cum into my mouth?"
"I don't see why not," I replied, and so I did. It was salty and tasted a bit like garlic.
"Taste the Italian? Not me, I'm Irish, but the food I had for supper last night."
"Yup," I said.
"Ok, you want a little pain, or just to get off?"
"If it is all the same to you, I am just ready to get off."
"Ok, lay back on the bed, I am going to put some whipped cream on you and lick it off, and hopefully, very gently, get you off at the same time. You are forbidden to touch your cock, but, when I am licking it you may play with your nips if you want." He put the whipped cream on my nips and a line down to my cock and balls, and proceeded to lick it off, starting with my right nipple, then my left, then my treasure trail, my balls, and finally my cock. It was the opposite of what I had done to him. At one point it was so gentle and I was so near to cumming, but I could not, without touching myself, that I said, "Ghost".
"This is torture," I said. "Torture that feels so good, but torture nonetheless."
He smiled and said, "There is more to S & M than brutal pain. You want to meet up again, there is a lot to explore. And there is a club that meets in a gym near Center City (as downtown Philly is known to the locals) once a month, if we do a few more sessions I think you might get into it and a good looking stud like you is always welcome."
"Maybe," I said, "I think I need to know more."
"How about I take you out to supper, do you like seafood?"
"Yes, and it is rare, if nonexistent, except for shrimp, in the college dining halls. But I pay my own way. I can afford it once in a while. If you pay, I feel like a whore."
"You've never done sex for money?"
"No, I came close in a bar down south one night, but it was mostly to see if I was attractive enough to do it if I wanted to, or had to."
"And, what happened?"
"A lot of guys came on to me, and a few women as well, but I went home with the guy who brought me there and had good free sex."
"Well, just supper as friends, and let me pay, the place is too expensive for a college student, and it will give me cred if any friends see me with a stud like you -- and if they ask, I will make it clear that you did it for fun, not money."
And with that we were off, had a great meal, I learned a lot about his life, sexual and otherwise, and he about me.