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Subject: Trip to the City-2 Trip to the City-2 Please support Nifty with your donations so we can continue to express and share our stories. Feel free to message me with comments or suggestions. Randy and I had continued to text since our tryst in the van. We devised a plan for me to drive to meet them. Even though it was a six hour drive one way, my horny 16yo self needed to do it. My parents were going to be working so they wouldn’t mind be away for an entire day. I got up early on that Saturday morning to leave. There was a text from Randy: “before you come make sure to shave off any pubes you have, shave your balls and shave your crack.” I was pretty smooth naturally so it didn’t take much. Since Randy was a soccer coach, I put in my T-shirt, gym shorts, black Nike shorts and tennis shoes then started my drive. About 30 minutes before I arrived, I got a text with an address and room number. I pulled into the parking lot of a cheap motel and circled until I found the room. I knocked and Randy opened the door wearing only gym shorts. He was 50 5’8 250 lbs. shaved head, red/gray mustache and goatee. His chest, stomach and shoulders was covered with red/gray hair. He had big round red nipples on saggy pecs and a beer belly. A real bear. He gave me a hug and said, “go in the bathroom and change into what’s on the sink.” In the bathroom on the counter was a white jockstrap. I stripped out of my clothes slid on the jock with my Nike socks and went back to the room. He was laying on the bed and motioned for me to come lay down. We lay facing each other and began kissing with our cocks occasionally touching over the shorts/jock. About 5 minutes in, there was a knock on the door. I jumped. “Calm down,” he said as he opened the door. In walked Bill and another man. Bill was 55 6’5 290 lbs. He had on a welders uniform shirt, jeans and work boots. He had salt/pepper hair and beard. He shook my hand introduced me to his friend. Fred was in his early to mid 60’s, 5’10 260 with white hair. He had on a dress shirt, slacks and dress shoes. He shook my hand and pulled a chair to the end of the bed and sat down. The room was almost dark with the curtains pulled and only light coming from the open bathroom door. The TV was off but the clock radio was playing music. Bill unbuttoned his shirt and tossed it on the floor. His chest, stomach and back were covered in thick salt/pepper hair. His nipples were pierced with steel studs and he had a barbed wire tattoo on each arm. He undid his jeans and pulled them off. I was mesmerized seeing him wearing only tightey-whiteys and white tube socks with red stripes. His cock was tenting the front of his briefs. Randy slid his gym shorts off, propped my head up and straddled my chest. manisa escort He had a thick red bush, 6.5 inch uncut cock avg girth and medium-size hairy balls. He began rubbing it on my lips. Bill pushed my legs apart and laid between them. I felt his tongue running up my leg and swiping between my legs. Then he started biting my cock through the jock. Randy said, “look up at me, open your mouth and stick out your tongue.” I did as instructed while he began rubbing his cock on my tongue. “Now, close your mouth on it and suck.” I did as told. “Look up and while you suck me,” barked. I stared up. “Is this your first time to have a cock in your mouth,boy” he asked. I nodded. He grinned. I looked over to see Fred had taken his cock out through his zipper and was stroking while he stared intently at us. Bill lifted my legs in the air and pulled the jockstrap off of me. I was now only in my black Nike socks. “Shit, Randy look back here at this pretty boy. He’s smooth as can be,” Bill said. Randy looked over his shoulder and reached back to get a feel and quick jerk on my 6.5 inch cut cock standing at attention. He looked back down at me smiling, “good boy” he said. He began to thrust his cock in my mouth causing me to gag occasionally. Bill sucked both of my balls in his mouth. He sucked on them, bit them and tugged then kinda rough. I grimaced and Randy grinned. He spit them and run his tongue from the base up my shaft on the underside to the head. He flicked his tongue a few times and then swallowed it to the base. He alternated between sucking and jerking it. Randy pulled his cock out and turned to face Bill sucking me. His hairy ass was now at my face. Randy pulled my spread legs in the air. “Damn just look at that smooth, tight boy hole,” said Bill. He buried his full face in my crack. His beard tickled as he swiped his tongue up and down my crack. “How’s it taste Bill,” Fred asked. “Like honey,” Bill responded. He licked for a few minutes then I felt him sucking my hole. His stiff tongue started to press inside and I clinched on it letting out a moan. Randy said,”I think he’s ready for it now.” Bill stood up and pulled off his briefs. He had an 8 inch uncut cock jetting out from a thick black bush. His balls were the size of two large egg hanging covered in hair. He had a steel cock ring around the base of his shaft and balls which made them look even bigger. He looked amazing standing there in only his red-striped white tube socks. He grabbed a bottle from the table and got on his knees between my legs. Randy still was holding up them spread open in the air. Fred undressed to his black dress socks and knelt on his knees on the bed next to Bill. His chest was covered in white hair, maraş escort white bush, small balls and his stomach and pecs were saggy. Randy and Fred watched as built scooted up to my exposed hole. I felt something wet run down my crack as he lubed up my hole and his cock. I realized now what was about to happen. Bill, old enough to be my dad, was about to pop my boy cherry with Randy, old enough to be my dad, and Fred, old enough to be my grandpa, watched. My stomach filled with butterflies and my legs were shaking. “Guy’s I’ve never done anything like this before. I’m not sure if I’m ready, ” I said. Randy reached back and patted my head. “You’re ready big boy. You’re about to become a man now. It’s gonna hurt like hell at first but when Bill gets his cock in, you’ll love it. We’re gonna take good care of you,” Randy said. It felt amazing Bill rubbing his uncut cock up and down my crack. His head stopped at my hole and I felt him starting to press. I immediately clinched. “Don’t do that, it will hurt more. Relax, take a deep breath and push out when he pushes in,” Randy said. I tried but I was tense. There was a pop. “Ouch, ouch, ouch,” I cried out. Bill moaned. “Shit I bet that felt good,” Fred said as he bent over for a better view. “Just relax, he just pushed the head in,” Randy said. “It kinda hurts,” I said. He reached back and patted my face. “It will at first boy but then you’ll open up and it will feel great,” Randy said. Bill held that position for a few minutes then I felt him push in more. “Ow, ow ow it kinda burns,” I said as I clinched my hole tighter. “That’s it boy, tighten your hole around my cock,” Bill said. Randy whispered something to Bill. He leaned his ass back in my face, “lick my ass boy,” he said. I stick my tongue in his hairy crack. Then, I felt a sharp pain. “Fuck that’s nice,” Bill barked out as he pushed the rest of the way into me. I tried to yelp but couldn’t with Randy’s ass on my face. Bill began to move his cock back and forth. “Look at his purple ass lips around your cock,” Fred said drooling as he stared at the cock in my hole. It continued to hurt as Bill started to slid back and forth. After about 10 minutes, he pulled all the way. Randy laid down in the bed with his legs hanging off the side. Bill pulled me up onto my bed and turned me around. “Bend over between his legs and suck him,” Bill ordered. I complied. Fred was on his knees beside Randy stroking himself. Bill walked up behind and used his foot to kick my legs apart. I heard him squeeze more lube on his cock, grab each of my hips and began pushing in. I had to start all over with the pain of being opened up. However, this time he just pushed right in so it went away faster. As I Randy, mardin escort Bill used a long and slow thrust rhythm in my hole. Randy moaned as I sucked. His balls were drawn up tight against him. He put his head on the back of my head and pulled me all the way down on him. “Shit,” he yelled out as I felt him shooting in my mouth. I was gagging and trying to get air but he held me in place until his last pump. I came up for air with a red face. “That was good boy,” he said. I was still bent over getting fucked by Bill from behind when Fred turned my head toward him, “open up and stick your tongue out”. Just as I did, “he began shooting his load in mouth. “Swallow my load boy,” he barked. Some landed on my face but most on my tongue and in my mouth. Bill was now thrusting hard. He held me in place by my hips as he began to go in deep. I felt a slap on my ass cheek. He began to spank me with each thrust. Randy and Fred were standing on each side of him watching. “Look at that red hand print on his pretty little white cheek,” Randy stared. Each one commented about how I was taking it. “You ready for my load, boy” Bill asked. “You ready for daddy to breed your boy pussy?” It hurt but felt good at the same time. I was loving having him inside me. “I’m going to tear you up boy,” he said. I could feel sweat dropping onto my back. “Fuck his little hole,” Fred said. I looked over and was able to see us in the mirror. I watched as Bill pounded the shit out of me. He fucked me for a good 30 minutes at various speeds until I felt him thrust all the way in and collapse in me. We feel to the best and his cock convulsed in my hole as I felt his warm load flood my insides. His ass pumped a good 10-12 times. “That was so hot boy. I hope your first time was amazing,” he said as he kissed my neck. “Yes Sir. Oh my god it was.” He lay there on top of me with his cock still inside. He stayed hard from the cock ring. He finally pulled out and stood up. “Spread your cheeks for me,” he said as I separated them. The three men stood and admired. Fred pokes at my hole which was sore. “Look at swollen his ass lips are. You popped his cherry good,” Fred said as cum oozed from it. Randy pulled off my socks and helped me up. Randy, Bill and I got into the shower with me in the middle. Fred was standing outside the tub and grabbed my hard cock and stroked. Bill and Randy nibbled my ears, kissed my neck and then both stuck their tongues in my mouth at the same time. Fred jerked my load that shot across the bathroom floor. He got dressed, shook all our hands and left. We finished our shower and they dried me off. Bill gave me a hug and a fist bump to Randy and left. We dressed and he walked me to my car. “I hope it wasn’t too much and you had fun,” he said. “I wanted to make sure your cherry got popped good the first time.” “Yes, sir. It was fantastic,” I said. “Let’s keep in touch and maybe meet for a third time,” he said. I drove away with a sore ass but a smile on my face.

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