"We can do this the slow, more comfortable way, or I can just fuck you right here right now and get it over with. Your choice." I said, looking him straight in the eye.
He flinched a little, but there wasn't any real hesitation; "Slow and comfortable, I think..."
"OK, take off your clothes, I'm going to go wash the dildoes." And I walked into the bathroom to wash my collection of rubber toys.
It had all started the night before. When I answered the knock at my front door, a nice looking college boy was standing outside. He identified himself as representing some kind of business fraternity, and that he was selling magazine subscriptions to support his scholarship. I really didn't listen too hard, as when I opened the door, his eyes had struck me in a very pleasant fashion.
He wasn't really paying a whole lot of attention to me, either, which I didn't notice (due to the mesmerizing eyes) until I realized that my TV Was showing hardcore boy on boy on boy porn (with the sound muted) and that my visitor was either fascinated or horrified. Having invited him into my apartment, I put the porn out of my mind, and concentrated harder on his sales pitch (such that it was) - I signed up for some random expensive magazine, then told him I had to go find my checkbook. At no time had I turned to see the TV, pretending I had no idea there was super XXX twink double penetration action fantasy taking place in my living room.
From the spare bedroom where I claimed to keep my checkbook, I yelled out and offered him a drink of some light refreshment, but he declined in a somewhat choked voice. I walked back into the living room and made sure to check his crotch, which had a nice looking swell to it. I finally pretended to notice the porn, and paused it, quite expertly, on a cumshot. I apologized profusely for any offense I may have caused, offering to perhaps purchase another magazine. He replied that they weren't allowed to sell more than one subscription per day to any particular customer, and made a polite exit.
He came back the next night. Thinking he would never come back again, I didn't have any porn cued up for when he knocked. But it became very was clear to me what it was that he wanted.
Returning from the bathroom with wet soapy hands, I found a rock hard naked college kid in my living room. I realized that I had missed a good underwear pervert moment, but figured I could just keep whatever clothing of his I wanted, he didn't seem the type to argue with authority.
"Show me your ID." I insisted - wanting to make sure I wasn't committing any kind of offense by offering to deflower him.
He rustled through his clothes and then handed over his Washington state driver's license and I looked it over closely. It said he was twenty, but he could have passed for a good seventeen. I gave him his license back, which he tucked into a pocket of his jeans.
"OK, for the slow and comfortable route, I'm going to slowly put larger and larger things into your asshole. I will be as gentle as possible, and it will hurt, but you have to cooperate with me, is that clear?" I was as non-patronizing as anyone could be, standing with an armful of dildoes in front of a twenty year-old naked man.
"I understand." He said simply, he appeared to be a boy of few words, but a willing playmate. I cued up a random porn movie and got to work on his ass.
Positioning a pillow in the middle of my living room floor, I directed him to lay on his back, with the pillow under his butt. As he moved into position, he oblingly held his own legs out of my way as I moved in for the first penetration. At this point, I wondered if he was playing me for a fool, but when I started on his hole, it became very clear just how much of a virgin he was.
"I am going to start by smearing lube all around your hole." I told him, squeezing lube into my hands and rubbing them together to make it warm. I started to work on his hairy little hole my feeding a well-lubed pinky over the tender membrane of his anus. I could hear his breathing get heavier as I slowly worked my way in.
"This works best if you train your ass to work with me." I peered over his crotch to meet his gaze - his face was pointed directly at me, and I wondered how his neck didn't get too tired, but carried on.
"As I push my finger inside of you, you must relax your sphincter against my insertion." He nodded an acknowledgment, and then complied perfectly with my instructions. It took a little bit of time, during which I heard him wince and sigh, I couldn't tell which was pain and which was pleasure.
"Excellent!" I congratulated him, I now had one pinky all the way inside his ass. It was going to be a long night...
I let him get used to the pinky, and spent some time surveying his body in detail. The boy's cock was a nice average size, with a nice purple head and a very uniform circumcision. As I felt him flex his sphincter against my pinky, his cock would twitch, and I could see his scrotum tighten slightly.
He had a nice body, not so lean that he looked emaciated, but in no way was he flabby. Looking at his chest, I imagined a couple of nipple clips, perhaps joined on a chain to a shiny cock ring... His skin was very lightly tanned, I could tell he wore boardshorts as he was white from his waist to his knees, he didn't have much in the way of body hair, but I was wondering about shaving his balls, or perhaps the peachfuzz around his hole.
"I'm going to slowly retract my finger now. Relax and just let it slide out." Again he nodded at my instruction. "Next up is going to be something a little softer, but more substantial." His eyes shot me a "what are you talking about?" look, so with my free hand, I waved a small silicone plug, which I then proceeded to insert inside him. I made sure to apply plenty of lube.
At about three inches long and an inch or so around, it wasn't going to hurt him. I slowly drove it home until the base nestled snugly against his cheeks.
"Sit up," I suggested, commandingly, "I want to watch you jerk off with your ass plugged."
He smiled, and gingerly slid his ass off the pillow, leaning against my couch. His legs were wide open, and his throbbing cock looked like it wouldn't take much to explode. I handed him a tube of lube and stepped back.
Sheepishly, he dribbled a small amount of clear lube on the head of his cock. He then rubbed the tip with his thumb and forefinger, smearing lube up and down his shaft. His eyes closed as he started to jerk really fast... I moved toward him and pressed a finger into the base of the plug in his ass and he came. A loud sigh followed by a thick stream of white liquid splattered across his torso. Then another, smaller eruption, and then one smaller than that. All the time I could see his sphincter muscles grabbing onto the plug in his ass and squeezing tight.
"Do I have to buy another magazine from you, or are you just coming back tomorrow night?" I asked...
He flinched a little, but there wasn't any real hesitation; "Slow and comfortable, I think..."
"OK, take off your clothes, I'm going to go wash the dildoes." And I walked into the bathroom to wash my collection of rubber toys.
It had all started the night before. When I answered the knock at my front door, a nice looking college boy was standing outside. He identified himself as representing some kind of business fraternity, and that he was selling magazine subscriptions to support his scholarship. I really didn't listen too hard, as when I opened the door, his eyes had struck me in a very pleasant fashion.
He wasn't really paying a whole lot of attention to me, either, which I didn't notice (due to the mesmerizing eyes) until I realized that my TV Was showing hardcore boy on boy on boy porn (with the sound muted) and that my visitor was either fascinated or horrified. Having invited him into my apartment, I put the porn out of my mind, and concentrated harder on his sales pitch (such that it was) - I signed up for some random expensive magazine, then told him I had to go find my checkbook. At no time had I turned to see the TV, pretending I had no idea there was super XXX twink double penetration action fantasy taking place in my living room.
From the spare bedroom where I claimed to keep my checkbook, I yelled out and offered him a drink of some light refreshment, but he declined in a somewhat choked voice. I walked back into the living room and made sure to check his crotch, which had a nice looking swell to it. I finally pretended to notice the porn, and paused it, quite expertly, on a cumshot. I apologized profusely for any offense I may have caused, offering to perhaps purchase another magazine. He replied that they weren't allowed to sell more than one subscription per day to any particular customer, and made a polite exit.
He came back the next night. Thinking he would never come back again, I didn't have any porn cued up for when he knocked. But it became very was clear to me what it was that he wanted.
Returning from the bathroom with wet soapy hands, I found a rock hard naked college kid in my living room. I realized that I had missed a good underwear pervert moment, but figured I could just keep whatever clothing of his I wanted, he didn't seem the type to argue with authority.
"Show me your ID." I insisted - wanting to make sure I wasn't committing any kind of offense by offering to deflower him.
He rustled through his clothes and then handed over his Washington state driver's license and I looked it over closely. It said he was twenty, but he could have passed for a good seventeen. I gave him his license back, which he tucked into a pocket of his jeans.
"OK, for the slow and comfortable route, I'm going to slowly put larger and larger things into your asshole. I will be as gentle as possible, and it will hurt, but you have to cooperate with me, is that clear?" I was as non-patronizing as anyone could be, standing with an armful of dildoes in front of a twenty year-old naked man.
"I understand." He said simply, he appeared to be a boy of few words, but a willing playmate. I cued up a random porn movie and got to work on his ass.
Positioning a pillow in the middle of my living room floor, I directed him to lay on his back, with the pillow under his butt. As he moved into position, he oblingly held his own legs out of my way as I moved in for the first penetration. At this point, I wondered if he was playing me for a fool, but when I started on his hole, it became very clear just how much of a virgin he was.
"I am going to start by smearing lube all around your hole." I told him, squeezing lube into my hands and rubbing them together to make it warm. I started to work on his hairy little hole my feeding a well-lubed pinky over the tender membrane of his anus. I could hear his breathing get heavier as I slowly worked my way in.
"This works best if you train your ass to work with me." I peered over his crotch to meet his gaze - his face was pointed directly at me, and I wondered how his neck didn't get too tired, but carried on.
"As I push my finger inside of you, you must relax your sphincter against my insertion." He nodded an acknowledgment, and then complied perfectly with my instructions. It took a little bit of time, during which I heard him wince and sigh, I couldn't tell which was pain and which was pleasure.
"Excellent!" I congratulated him, I now had one pinky all the way inside his ass. It was going to be a long night...
I let him get used to the pinky, and spent some time surveying his body in detail. The boy's cock was a nice average size, with a nice purple head and a very uniform circumcision. As I felt him flex his sphincter against my pinky, his cock would twitch, and I could see his scrotum tighten slightly.
He had a nice body, not so lean that he looked emaciated, but in no way was he flabby. Looking at his chest, I imagined a couple of nipple clips, perhaps joined on a chain to a shiny cock ring... His skin was very lightly tanned, I could tell he wore boardshorts as he was white from his waist to his knees, he didn't have much in the way of body hair, but I was wondering about shaving his balls, or perhaps the peachfuzz around his hole.
"I'm going to slowly retract my finger now. Relax and just let it slide out." Again he nodded at my instruction. "Next up is going to be something a little softer, but more substantial." His eyes shot me a "what are you talking about?" look, so with my free hand, I waved a small silicone plug, which I then proceeded to insert inside him. I made sure to apply plenty of lube.
At about three inches long and an inch or so around, it wasn't going to hurt him. I slowly drove it home until the base nestled snugly against his cheeks.
"Sit up," I suggested, commandingly, "I want to watch you jerk off with your ass plugged."
He smiled, and gingerly slid his ass off the pillow, leaning against my couch. His legs were wide open, and his throbbing cock looked like it wouldn't take much to explode. I handed him a tube of lube and stepped back.
Sheepishly, he dribbled a small amount of clear lube on the head of his cock. He then rubbed the tip with his thumb and forefinger, smearing lube up and down his shaft. His eyes closed as he started to jerk really fast... I moved toward him and pressed a finger into the base of the plug in his ass and he came. A loud sigh followed by a thick stream of white liquid splattered across his torso. Then another, smaller eruption, and then one smaller than that. All the time I could see his sphincter muscles grabbing onto the plug in his ass and squeezing tight.
"Do I have to buy another magazine from you, or are you just coming back tomorrow night?" I asked...
