Trevor:
Mike whispered in my ear, "You ready for it now?"
I shivered a little, both out of fear and out of excitement.
"Should I get a rubber?" I asked, thinking about how many girls this guy had probably fucked at the college.
"You got one?" He asked. "Yeah, go ahead if it'll make you feel better. But hurry up."
I scurried off of him, as he massaged his boner. I took another look, imagining it stretching out my hole, then ran down the hall to the bathroom.
I knew where Ivy kept her stash of condoms, and I also wanted to shoot some extra lube up my hole before starting down this adventure. I pulled a rubber out, tore open the package, and propped my bare leg on the side of the bathtub to shoot some lubricant up in side of me. I stopped and fingered my hole, thinking about Eric, and how much smaller his dong was than Mike.
"Hurry up in there!" Mike bellowed from the room.
I jumped, then hurried back to the room, stopping at the door. He was still jackin his pole. He glanced up- "Is this your first time to get screwed?"
I thought about my time with Eric, but figured that didn't completely count- plus I didn't wan't to confess to that right now, anyway, so I said, "Yeah...it's my first time."
"Are you scared?" He asked with a smirk, rubbing his cock.
"Yeah, a little." I answered truthfully.
"I thought so. Ok, let's just call it off," he said, throwing the blanket part way over his body and acting disgusted. "I won't make you do something you don't want to do."
I panicked, not knowing if this was for real or not. "No,...I mean, yeah, I'm a little nervous, but I want to do it..."
"Do what? What do you want to do?" He asked.
"You know," I answered, "Do it."
"No, I don't know...do what?" He asked, toying with me.
"I want you to, you know, screw me. Fuck me up the ass," I answered, blushing.
"Are you going to let me go all the way in?" He asked.
"Yeah, I guess so," I answered, almost in tears.
"Are you going to cry, or scream, or beg me to quit?" He demanded.
"No, I'll try not to," I answered.
"You ever wander what the virgin high school cheerleader feels like, when the varsity captain takes her out, and she knows what he wants? That he wants inside her panties to drill her? To pop her cherry? How nervous she feels when he drives down that dark country road and turns off the car engine- and she knows where it's leading....he pulls her hand over to his pants and unzips,"
"She always thought a dick would be about the size of a a finger, but she feels this hard piece of flesh with a sponge head on the end, and a bag of balls...and she thinks, 'that thing is going inside my body in a few minutes.' And then he is on top of her, and she can't say no now, she's went too far....and he's pushing and poking that thing into her, trying to find the hole....then he finds it, and it starts snaking it's way inside of her, and she feels every inch of it, with his tongue inside her mouth and on her neck...." he paused, and stared at me, "And then he breaks through and it's in up to the hilt, and she feels his balls slapping her...then he starts pumping like a big piston, splitting her in two, and she wanders how long it's gonna last, and what will happen when he reaches his climax- what it will feel like to her, him shooting that white stuff into her."
"And she smells him, a mixture of cologne and some sweat, and she feels his back as it arches over her. He's grunting and groaning and panting..." Mike smiled at me, "that's what your about to feel like. Like that girl, with me pushing inside of your body. Are you gonna like that?"
I gulped, feeling so excited that I was about to shoot a load standing in the doorway. I felt like that girl, about to have my cherry popped. I didn't care how much it hurt, I wanted him inside me.
"Come here," he said, reaching out his hand as I shyly stepped toward the bed.
He surprised me by taking my hand and gently holding it, then pulling it to his face. "Come here," he moaned, "Lay down next to me."
As I laid down, he said, "get on your right side." I lay down, and he snuggled up close to me, with his cock pushed into my crack. He kissed the back of my neck and my ear, and whispered, "you taste good, Trevor."
I could feel his cock slowly pushing between my buns- it didn't feel too bad. I knew he was searching for the hole, and I just hoped he would go slow.
He continued nibbling at my neck and ear when his dickhead found the spot. He reached down and pulled my buns apart, and pushed a little harder. I winced, as I felt it start to penetrate. He continued the pressure and said,
"Push back toward me, and blow out of your mouth like you're blowing through a straw."
I felt it go a little farther through, then a sharp pain hit, like something was tearing or ripping. I let out a yelp.
"Sorry about that, I'll slow down," he whispered hoarsely, as he continued to push harder. "Try to spread your legs some." I pulled up my left leg, and instantly he sunk deeper. I now felt like I was being impaled. There was a dull pain, and I felt like I was slitting in two. I felt tears in my eyes.
"On the count of three, I'm going to push it the rest of the way in," he whispered, "One, two..." I braced for the worst. "two and a half, two and three quarters.....are you ready?"
"Yeah, I grunted, go ahead."
"Where was I? He groaned....oh yeah, I was on THREE!!!" As he said it, he shoved as hard as he could, and I couldn't help but scream out, as it took my breath away.
"I'm in, you pussy," he laughed, "all the way."
I could feel his balls against me, and I thought for a second, 'he's stuck, he'll never get that out of me without pulling out my guts...' But he started pulling out, and it felt like I was taking a major shit. When he was almost out, I thought that it was over, but he rammed it all the way back in, and I grunted loudly again. I remembered that I had left the condom on the nightstand.
"You must have used some lube, kid....you're tight, but I'm sliding right in!" He laughed, rolling me onto my stomach, and rolling on top of me. "Let's pretend I'm that varsity high school captain, and your the little cheerleader getting her cherry popped, ok?" He pushed in and out several times, then pulled my ass up to the air so my back was arched and my knees were bent. I buried my head into the pillow.
"Now you're loosened up a little, are you READY TO FUCK?!" He laughed, and shoved in as deeply as he could go.
My mind was swirling, as I felt a mixture of pain, intense pain, even, but wild sexual feelings. I did feel like that virgin girl giving pleasure to her stud. I wandered what it would feel like when he got ready to shoot his load inside me. And he kept pounding in and out.
"You are so tight. I've never had a girl this tight in my life. You're squeezing the juice right out of me," he laughed, as he continued his pumping, and rocking me back and forth on the bed. He pulled my legs further apart, to allow himself to go as deep as possible, and I felt his ballsack slapping me with every thrust.
"I'm getting close to shooting," he moaned, grabbing my legs and squeezing them as he pumped. "I'm going to flip you over in a second, so get ready..."
In an instant, I felt him pull out, leaving a gaping hole, and grab my feet and flip me over. He was now straddling me, with his dick over my face.
"Open your mouth!" He shouted, "Now, open up."
I obeyed instantly, not thinking about what was happening, until a huge load of spooge sprayed across my face and into my open mouth.
"Eat it, eat it," he grunted, as he jacked off in my face. I was scared to close my mouth, but it kept filling my mouth until I was going to gag, so I had to shut it for a minute to swallow all of the goo. It continued shooting into my nose and forehead, and onto my hair.
As he subsided, he pushed his cock into my mouth. "Clean it up," he ordered, as he straddled my head. It had a weird taste to it, probably from the lube, and it was still leaking.
I did the best I could, as I felt it get softer and softer, until it felt like a mouthful of skin, along with the jism and spit. He pulled out, and rubbed it into my hair and pillow, before laying down next to me.
"How long are you here by yourself?" he asked.
"Umm...all day, I guess." I answered.
"Then I'm going to take a nap," he said, yawning. "You can sleep with me if you like, or do whatever you want."
I rolled over, and snuggled into his chest. I could feel the hairs of his armpit, as he wrapped his arm around me.
"You got stuff in your hair," he said, teasing.
"Yeah, that's ok," I said. "It'll dry."
I felt like his little cheerleader as I drifted off to sleep.