Bar Night with an Old HS Friend

I walked out of the bathroom and looked around for my clothes. I found my boxers and went to put them on.

"What are you doing? Come lay back down"

John is still naked, laying on his back. His cock is flopped over on his leg, I can't help but look at it. "I really need to leave."

"No, you don't. Come lay down." John says as he pats the spot next to him.

Once again, against my better judgement, I walk to the side of the bed and lay down. I roll on my side with my back to John.

He rolls over in my direction and I feel his hand on my waistline. "Did you enjoy last night?"

I take a deep breath. "I did. Not sure how I feel about right now though."

He rubs his hand along my side and whispers in my ear. "It's not a big deal, just two friends having fun." He inches closer to me and his hand moves over my cock. I can feel his cock resting against my asscheek. He starts massaging my cock.

"I really need to take off," I say to him. Unfortunately my cock responds to his touch and starts growing in his hand.

"It feels like you want a little more." He slowly strokes my cock which has now reached full erection. I can feel his cock getting hard as it pushes against my ass. It slides along my crack and between my legs, he continues to pump my cock. "This feels good, doesn't it?"

"It does, it feels really good," I say in between heavy breaths.

John moves closer to my ear and whispers, "would you like to feel my cock slide into your asshole?"

Just hearing the words sends shivers down my spine. That would be so hot, but I don't think his cock would fit in my ass. Plus I have already done enough exploring, that is an area I cannot explore. "It sounds hot, but I can't do that."

"Sure you can," John whispers to me. He takes his hand off my cock and rolls the opposite direction in the bed. I hear him grab something and then roll back against me. I hear the lube bottle and then a cool sensation on my asshole.

I gasp when his finger enters me and whisper out, "I can't do this. I'm not ready."

"Haha, you are ready." John laughs. "I have two fingers in your ass right now, my cock will fit perfectly."

"I....I can't....uuh....uuh...why does it feel so good," I stutter out.

"Reach your hand for the nightstand drawer," John says and I reach out and pull the handle. "Grab the box and hand it to me."

I take the box and notice they are magnum condoms for large size. I just hold them in front of me, contemplating what is about to happen.

John scoots down the bed. He grabs my leg and rolls me over on my back. His fingers still in my ass. My hard cock flops down on my stomach. John is kneeling between my legs, his enormous cock pointing right at me. "Hand me the condoms."

John takes the box and slowly removes his fingers from my ass. He takes a condom out and rips apart the wrapping. I watch as he puts the condom on his head and rolls it over his shaft.

I start second guessing this act, "John I don't think this is a good idea."

He says nothing, I'm not sure he even heard what I said. He squirts lube on his cock and strokes his fingers around to rub it in. Then I feel his fingers massage the lube around my asshole. John grabs his cock and places it at the entrance of my asshole.

"Jim, relax your muscles. This might hurt a little." I feel his head penetrate the hole. "Nice and easy, thats it."

His cock moves further. I can feel my hole opening up, but it doesn't hurt like I thought it would. Or maybe I enjoy the pain.

"Oh fuck, thats tight." John says as he uses his fingers to push his cock deeper. He looks down at me, "does that feel okay?"

I look back at him, "it does. It feels good."

John looks back at his cock and pushes it in a little more. "Fuck, I'm deep. Your ass feels good" He leans back a little, and grabs hold of one my legs. Slowly he starts pumping his cock into my ass. I lean my head back and close my eyes.

He starts moving at a steady pace. The feeling is uncomfortable, but I am starting to enjoy it. I start moaning in unison to his pumps. I reach out and grab hold of my own cock.

"Look at me Jim," he commands. I open my eyes and look at John. "Dude, your ass feels so good."

"So does your cock," I moan back. "I can't believe how good it feels."

John grabs my other leg, bending my knees towards my chest. He places his hands on the back of my legs, giving him more leverage to push into my ass. His muscles are flexing and his pace begins to pick up speed.

I am on the verge of orgasming and start jerking my cock. John notices. "Yeah Jim, stroke your cock. You like my cock in your ass, tell me you like it."

"Fuck, fuck that feels good!" I scream out. "Your cock feels so good in my ass!" I hold my cock as jets of cum explode from the tip and land across my stomach.

"Yes, yes. I'm cumming too!" John pumps a few more times, I see his eyes wince and he stops pushing. "Oh man, that felt good." He gives a couple more pumps, finishing his orgasm.

He slowly pulls his cock from my ass and climbs off the bed. My feet drop and I roll over on my side. He slaps me on the ass, "good job, that ass felt great."

I smile up at him, his cock pleasured me and my ass gave him pleasure. He walked into the bathroom and I heard him he remove the condom. I rolled off the bed and could feel discomfort in my ass.

"Are you sore?" John asks as he walks back into the room.

"Yeah, a little bit. I felt okay in bed, but standing is difficult."

"As you move around it will get better," John says. "The first time is always the worst, it will get easier."

I slide my boxers up, then my jeans. "This is it, I will never do it again."

John hands me my shirt and says, "thats not true, your love for cock will bring you back."

I put my shirt on and start gingerly walking down the hallway. I yell over my shoulder, "No way man, my ass is too sore. I had a good team, but that is all the cock I need."

I hear John laugh from his room and then he yells back to me, "hang on, let me give you my number. On the off chance you want it again."

He meets me at the door, still nude with his cock swinging freely between his legs. He hands me a sheet of paper with his number on it and looks me in the eye, "one more time, get down on your knees and blow me."

"Are you serious?" I question, but he just stares at me. Without an answer, I get down on my knees and reach for his cock.

John grabs my hand, "I was kidding. I knew you had a love for cock." He opens the door for me to leave. "Don't turn into a cock whore around town."

I walk out the door feeling somewhat rejected, but I can't help feel compassion for John. He's right, I will be back.