True Story First Time

It was the Saturday night before the 4 day Thanksgiving break. We started wrestling practice that Monday and there was a big party at my parents house celebrating the oncoming season. All the wrestlers and their parents were there. Bored, I asked two friends if they wanted to see some porn I had upstairs. They quickly agreed and we went upstairs to my room and locked the door.

I had some magazines of girls sucking big cocks and getting fucked in the pussy and the ass. My buddies and I were loving the pics and I asked if anyone wanted to play strip poker. It seemed random to ask but one of my buddies said he and his brother played it over the summer in their yard and the loser had to streak naked around the outside of the house. It seemed innocent enough. 

Only, we didn’t have a house to run around like in the summer. So there really wasn’t any “punishment” for the loser. I was only 16, as were my buddies and none of us had any idea what to do. I don’t know how I had the balls to say it but I did, and I said, “Why don’t we play strip poker?”

My friends went along with the idea but it seemed like they weren’t into it. We played Black Jack as none of us knew how to play poker! 

“I know, why doesn’t the loser jerk off? It just came out of me. Matt and Sean mumbled in agreement. 

We all were losing hands and before you knew it we were all down to our underwear.  My friend Matt seemed like he thought the whole game was stupid. When I looked over at my friend Sean, well his cock was rock hard, stretching out his underwear. He looked at me noticing I, too, was hard. 

Matt lost the next hand and went in the corner and pretended to jerk off. He was soft and uninterested and started looking at my bookshelf.

Sean and I played the last hand. I wanted to lose so I could jerk off in front of Sean. Naturally, I won. Sean pretended to jerk off too. I said, “Well fuck it! I might as well jerk off!”

And so I did. I pulled off my jockey shorts and opened my legs wide so my dick, balls and asshole could be seen by Sean. He sat across from me staring at me as I jerked off. Matt was still face deep in my bookshelf.

I stroked my cock as Sean stared at me. I was so horny, and so hard I came quickly and shot a huge load all over my stomach. Sean just stared at me the whole time, not saying a word. 

I cleaned up and said, “Let’s go back downstairs to the party.”

Matt said, “Yeah, let’s go. And let’s all promise we never talk about this or ever tell anyone.” Sean and I agreed and were equally paranoid about someone finding out what we had just done.

Being a short week at school as we only had 3 days before Thanksgiving, after wrestling practice that Wednesday I got home and had dinner and was going to chill. 

Then something happened that changed everything. The phone rang. 

“Hey Phillip, it’s Sean.” 

I was thinking, “What?!!!”

“What are you up too?”

“Nothing”, I said. “You?”

“Not much. Want to come over?”

Needless to say, I was stunned. And very turned on.

“Absolutely. I’ll be there in 15 minutes.”

“Awesome”, Sean said. “See you soon.”

I hung up the phone with my cock rock hard. I grabbed the car keys and told my parents I was going to Sean’s house.

When I got there there was only his brother Dave in the house. Sean told me we’d hang in the TV room with his brother. We sat there for only about 10 minutes when Sean turned to me and asked, “Want to go up to my room?”

“Sure”, I said, trying to be cool about it.

Sean got up and left the room and I followed. As we walked upstairs I was staring at his hot ass the whole time. We got to his room and I didn’t know what to expect. I was checking out his room when he said, “Wanna play cards?”’

Damn! He’d enjoyed the other night and brought me here for more! How much more?

“Sure”, I said, trying to be cool about it. He sat down on the floor. So I did. He then asked, “Want to play strip poker?”

“Sounds cool to me!” And Sean started dealing the cards…blackjack again!

“What does the loser have to do this time?”, I asked.

“Anything the winner wants”, he said and grinned at me. 

Sure enough we got down to our pants and underwear. He lost the hand and took off his pants. He was rock hard again. I lost the next hand, took off my pants and we were both rock hard.

“Final hand”, he said, and grinned again. A few days ago I wanted to lose so I could jerk off in front of Sean and Matt. Now I wanted to win. Only this time, I lost. 

I looked at Sean, “Well, you win. What do you want?” 

He just smiled at me but said nothing. It was up to me to say it. But what if I was wrong? Fuck it. I didn’t care.

“A blowjob?”, I asked.

He nodded.

“Okay. But you have to give me one too. And you can’t tell anyone.”

He went over and locked the door to his room, and then said, “Where do you want me, stud?

“I don’t know. On your bed?”

“Why don’t we start with me in this chair.”

“Okay. But you have to take off your underwear.”

“Fine. But you have to take off yours too.” He took off his underwear and so did I. I’m about 6.5 inches, a cut, fat cock. He took off his underwear. His cock was huge. Probably 8” x 6”. I felt stupid with my dick compared to his.

He sat back in the chair, his hard cock pointing in the air. I kneeled down in front of it, not believing what I was doing but not wanting to stop either. I grabbed his big fat cock, looked up at him and said, “You can’t tell anyone and you have to blow me too.”

“I won’t tell anyone”, he promised. Looking back who would he tell? “And I’ll blow you. I promise.”

With that I took the head of his cock in my mouth. I started sucking and heard Sean moan. I pulled his big dick out of my mouth licked up and down and then went back down on his huge cock. He moaned with pleasure and told me take his whole cock down my throat. I tried but being the first time giving head, and to a big fat dick, I was struggling. He then started fucking my mouth and I opened wide as he lifted up his ass from the seat and fucked my mouth deep. The whole time I was jerking my cock as I was rock hard. He slowed and I pulled his cock out of my mouth and spit on it before sucking it fast and hard. I then took his cock out of my mouth and started sucking and licking his balls. I then let my tongue flick down near his asshole, seeing if I he would like it. He pushed his ass out over the chair as an invitation to further lick his smooth hole. I could smell he had cleaned up before I arrived, anticipating that I might try to lick his sweet hole. And boy did I. I had seen and read enough porn to try to be a good ass eater and I loved it. I started by lightly licking his hole, teasing him. Sean moaned and said, “Yeah, Phillip, eat my ass!” 

He then reached behind my head and pushed my face into his asshole. It turned me on so much I ate his hot ass with everything I had as I moaned. I pushed his legs back and he responded by spreading his legs wide so I could open his hole and tongue fuck him and spit on his asshole. It was so fucking hot for both of us.

Sean stood up and moved me to the bed telling me to lay down. He got on top of me, spread his ass cheeks and sat on my face telling me to keep eating his ass. He then bent over and started sucking my hard cock. I was fucking moaning so loud as he moved his ass all over my face and up and down on my tongue. He seemed to love my cock too as he deep throated it then pulled it out and stroked it. I told him I was going to cum and he started sucking and deep throating me which only made me get closer. I’m cumming I said, almost as a warning. He didn’t care and I shot maybe the biggest load I ever had and he took it all and swallowed every bit of my cum. 

He then moved to the front of the bed and picked my head up and guided his cock to my mouth.

“Now I want you to swallow my load.”

He then took his fat cock and started face fucking me and quickly started to say he was cumming. He held my head as his load shot down my throat. I swallowed it all thinking it tasted pretty good. Sean then lay down beside me and we lay there for a little while. 

I realized I needed to get home so I said, “I hope we can do this again soon.”

Sean agreed and said, “Absolutely. There’s more I’d love to do with you.”

I responded, “Sounds good to me.”, as my cock started getting hard again.

Wrestling season went by, then spring and the end of school. Sean hadn’t spoken to me that much and not about that night. I was really bummed but didn’t push it. I figured it was a one time thing. 

The day after school ended I was just chilling and feeling grateful I didn’t have to deal with school when the phone rang.

It was Sean.

“Hey Phillip, what’s up?” I was immediately hard. I tried to act cool and non-chalant.

“Not much. Just psyched school is over. How about you?”

“Nothing. Just chilling. So, you have plans today?”

My cock was twitching in my jockey shorts.

“Naw. No plans. I’m totally free. You?”

“The same,” Sean responded. “Want to come over?”

I couldn’t believe it. 

“Sure! That would be great!”

“Cool”, he said. “No one is home.”

“That’s really awesome,” I said. What a moron I sounded like.

“Well, when can you get here?”

“I’ll just jump in the shower and be right there.”

“Great. See you soon.”

I showered, got very clean, and wore some blue jockey shorts I thought, at the time, were hot.

I got to Sean’s place and we went right upstairs. He had a porno magazine. He showed me this guy’s cock. “Mine’s bigger.” If I were quick and not 16, I would have said, “Yeah? Prove it.” Instead I just said the guy in the picture had a nice cock. 

Sean just said, “Want to play strip poker?”

“Yeah”, I said as we sat on the floor.

“Loser does whatever the winner wants”, Sean said.

He had gotten more comfortable with me and I with him. Soon enough we got down to our jockey shorts with our raging hard-one.

“Nice blue jockey’s”, he said. 

“Thanks. I wore them for you.”

He smiled. “I like that.”

I didn’t care if I lost when I did.

“Take off your underwear,” Sean said.

I did.

He leaned forward and we kissed. It was a deep French kiss that most certainly surprised me and my hard cock rubbed against his hard cock in his underwear. He then pushed me down on to the floor as I took his cock out of his underwear. His cock popped out and I pulled them down so he could step out of them.  

I immediately grabbed his big, fat cock and started sucking it. I was hungrily sucking his hot tool fast then slow, then trying to take it all. Then I focused on his head and licked around it and then just sucked the head for a bit before picking up the pace and sucking his cock fast up and down. Sean moaned loudly loving it. 

He then pulled me up and laid me down on the bed. He got on the bed, straddled my face, reached back and spread his ass cheeks open and put his hole on my face. I was eating his smooth hole and he started rubbing his ass all over my face then told me to tongue fuck him. He leaned over and started sucking my cock and fingering my ass. Then he moved off my face and went down to suck my cock and eat my ass. He spit in my hole and tongue fucked me and then told me he wanted to fuck me. 

I told him yes, please. But go slow. I’m a virgin. He promised he would. Then he pulled out some lube put some on his hard cock and told me to put some up my ass. Then he told me to move it around with my fingers so it would open up for his cock. 

He was very slow, very gentle. Then he said he was going to start and moved his dick up to my hole and slowly put in the head. As soon as he went further it hurt like hell and he pulled out and ate my ass some more. Then he asked if he could try again. I said yes. He leaned over and gave me a long, deep kiss. I moaned. He then slowly moved his cock up my ass and it hurt again but then the pain eased and he eased his cock inside me as I mosned with pleasure.

“You can be loud, Phillip. No one is home.” I mosned louder as he started moving faster, checking to see if I was okay. 

Finally I said, “Fuck me, Sean. Duck me as hard as you want.” He started pounding me and I was so turned on I started bucking up to meet his cock. He moved back and spread my legs open and ponded me more then held my ankles and let loose on my ass. 

“Fuck, Sean. You’re amazing!”

“You are too, Phillip! You’re so fucking hot! I’m going to cum. Can I cum inside you?”

“Yes”, I said, breathless, and he then moaned or yelled as his cock started spurting up my ass. 

“Ohhhh fuck Phillip!” His cock was drained into me, so much cum. He pulled out but then went back inside fucking me even more. Then without even touching my cock he looked down and I shot stream after stream of cum out of my cock. Then he pulled my cock up and caught a stream in his mouth and swallowed it. Then I finished full of his cum, and covered in mind, Sean stayed inside me and laid on top of me kissing me. It was amazing. 

He whispered in my ear, “I want you to spend the night.” I did and we each came 4 more times and played for the next 2 years until we went off to college and drifted apart. 

I still want him to this day.