I was sitting in my favorite gay bar one evening, downing a couple of beers and unwinding after a hard day at work, when I overheard a young guy on the stool next to me lamenting about the sorry state of the world. "And besides, politicians are all crooks," he said to nobody in particular, as he recited a litany of complaints to the bartender, a litany I tended to mostly agree with. Until he turned my way suddenly and blurted out, "and now with AIDS my generation can't even have fun with sex anymore... " I raised an eyebrow. "I'll never know what it's like to have my butt plowed really good," he dropped his head and moaned into his drink.
Well this was too much even for me. I took a quick swig of my beer, set it on the bar, looked at him and smiled. "So you wish you could have your ass plowed?" I asked with a sly grin.
"Yeah," he said, "but you can't do it by playing safe." He seemed to be throwing down the gauntlet. I couldn't resist.
"What if I prove to you that you can?"
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"What do you have in mind?" he asked, a little warily.
"Come up to my place and I'll show you," I responded, throwing the ball back into his court.
He paused, gave me a long cold stare, as if trying to read my thoughts, then a slow smile began tugging at the sides of his mouth. He stood up, grabbed his jacket and said, "Ok, stud, prove me wrong!" I asked him his name. "Joey," he said.
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"John." I offered my hand and we were off.
When we got to my place I offered him a glass of water. "You're not one of those manics who chop people up and hide their body parts in the freezer to munch on later are you?" he joked self-consciously. I laughed. "Don't worry, I'm a vegetarian." We both laughed. "Now what's this about plowing my ass?" he asked, still tipsy from the drinks he'd downed earlier in the evening. In the brighter light of my apartment I could see how young he really was, no more than 18 or 19 I surmised, with clear olive skin and dreamy blue eyes.
"I want to prove to you we can practice safe sex and still give your butt a real workout," I replied. "At least that's what I thought we agreed on."
I could see the lump in his crotch starting to push upward. "Like I said in the bar what do you have in mind?"
"Well, we can start with this," I answered, and leaned over and pressed my lips against his. Instantly his mouth gave way to my tongue and we found ourselves exploring each other's mouths. His breath had an odd yet agreeable taste of whiskey and breath mint, sweet and tangy, as I moved my tongue around his gums and pressed against his teeth. He grabbed for my crotch and I reached under his shirt to massage his nipples with my thumb and index finger. Before long, we found ourselves naked on the couch, exploring each other's bodies. I wet my finger and slid it into his ass.
"Oohh that feels good," he said, as I finger fucked him.
"You have a nice tight ass," I said, and gently poked a second finger up his hole.
"Yeah, do it," he whispered in my ear. I turned him around and finally had him across my lap. "Now this gives me a really good view," I said, slapping his ass cheeks playfully with my hand. He had the most beautiful ass, smooth muscular cheeks with a line of dark brown hair running from the base of his spine, making a circle around his pink puckered hole, and continuing to the bottom of his balls. I leaned over and buried my face in his crack, taking a long whiff of his musky crotch and tonguing his hole.
This got him very excited as he pushed up against my face. "Oh man, yeah," he moaned.
I stood him up, smiled at his strong youthful body and led him off into the bedroom. As he layed down on the bed, I put a rubber on my pole and lubed it up with gobs of K-Y, next I spread his legs high in the air and began to apply the lube to his hole. His buns tightened as the cold K-Y touched his ass and I saw him gazing somewhat apprehensively at my shiny erect latex covered hardon.
"This is your first time?" I asked.
"First time ever," he replied a little nervously.
I smiled. "Lie back," I said. "Just relax."
"I was told the first time always hurts," he said.
"Then why were you wishing to be plowed back at the bar?"
"I never really thought anyone would take me up on it," he said. "And after a few drinks I didn't really seem to care."
"Until now ..." I replied watching him gazing at my dick. He seemed to be mentally measuring the circumference of his asshole against the size of my cock head to try and figure out if it would fit. He seemed to be having major doubts.
I again touched his lube coated ass with my finger. Again, his buns tightened. I thought for a moment. "Maybe we can try something else," I said, playfully rubbing my chin. "Wait right here, don't go anywhere."
"Can I lower my legs?" he asked innocently.
I grinned. "For the time being."
I went into the bathroom, returning shortly with an enema bottle filled with warm water. Joey raised both eyebrows when he saw what I had in my hands.
"Hey I don't know about this," he protested halfheartedly, but I bent over and kissed him on the mouth and stroked his short brown hair. "Not to worry," I said, "not only is this not going to hurt in the least but it's going to feel reallyreally* good."
I spread his legs again, and touched the tip of his hole with the tip of the enema tube. He asshole puckered a little. I began massaging his cock with one hand as I held the bottle and tube with the other. Slowly, surely, his erection returned, and before long he was closing his eyes and moaning softly. I slowly relinquished his cock to his own hand, and very gently began to insert the enema tube into his asshole. His hole at first closed around the tip, but then finally gave way, and the tube slid in several inches. His moaning increased. I raised the bottle up above him and the water quietly flowed down into his hole.
"Oh man," he groaned as the bottle emptied its contents into his gut. When it was empty, I pulled the end of the clear plastic tube off the bottle, and inserted it in my mouth, sucking the water that had entered his ass back out and up the tube until it had nearly reached my mouth. Then I blew into the tube and the now murky brown water went back into Joey's ass.
"God, that feels good," he moaned.
"You like that?" I asked.
"Yeah, it feels like I'm being massaged from the inside out." Then he added, "please don't stop."
I didn't. I alternately sucked and blew on the tube over and over, causing Joey to squirm in obvious erotic delight on the bed. "I've never had my insides worked like this," he said, his hands rubbing his ass cheeks and his cock flapping stiffly between his legs.
As he squirmed even more, he began to moan that he wanted my cock up his ass more than anything else in the world. I blew the last drops of ass water back into him, and told him to go to the bathroom and relieve himself. He got up and ran quickly but carefully to the john. I could barely suppress a chuckle at the sight of him hightailing it across the room half bent over and his thighs rubbing close together as if he were trying to keep the middle part of his body from falling out into his arms. When he returned, he readily jumped back on the bed and spread his legs high and wide. This time as I lubed up the condom on my erect cock, he smacked his lips at the sight. I knew the enema had sufficiently loosened him up for a good fucking.
Leaning over him I slowly pushed my cock against his hole. "Now tell me if this hurts," I said, as his sphincter sprung open and the head of my dick slid in.
"Oh no," he said, "it feels good. Yeah, fuck me," he nearly pleaded, as I began my slow rhythmic motion in and out, his ass enveloping my cock like a warm moist glove. I started pumping faster, and harder, pushing my cock up to my balls. "Fuck me hard," he moaned, and in perfect unison my thrustings were met with equal thrustings of his pelvis against my thighs. Finally, I was plowing Joey as hard as I could, and he was taking each and every thrust with equal abandon.
"I'm going to cum," I cried out.
"Yeah, shoot that rubber full of cum," he encouraged me, as if I needed any encouragement. My cock was straining hard against the latex as I shot stream after stream of hot creamy liquid into the nipple of the rubber, and Joey cried out as he stroked his cock faster and faster and a long steady stream of semen hit me on my face and dripped down my chin and onto Joey's stomach.
"God," was all he said as his eyes rolled back in their sockets and he sighed deeply. I fell forward to bury my face in the cum on his stomach. I think Joey had finally found religion.
After we'd taken a shower together (where I was able to get Joey off a second time within several minutes by jerking off his soapy rod) he dressed, and got ready to leave. "Oh, by the way," he asked, just a little sheepishly, "do you have any other toys to poke my ass with?" I scribbled my phone number on a piece of paper and handed it to him. "There's only one way to find out," I replied. He took my number and smiled, carefully folding the piece of paper and sliding it into his wallet.
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