First time, Older Guy

It was gym, first block on a monday. We were playing a relatively uneventful game of Softball as most people were still half a sleep. Early in the game I got an in the park home-run. After getting of the field I headed to the water fountain for a drink. As I approached the water fountain I saw one of my brothers senior friends (I was just a freshman).

'Hey what's up Dave?' I said as i came closer to him

'Hey Russell. Nice job. First one to get a run.' he said as he bent down to get a drink. I stepped in line behind him waiting for him to finish.

All of the sudden he turned around quite fast. He stood there for a second then he pulled out the elastic on my shorts, stuck his hand down and grabbed my cock and balls. He stayed there for a second then pulled his hand out, gave an approving nod, and walked away.

I didn't know what this meant and thought it was probably just some senior freshman thing. At this age I had begun realizing that I liked guys more then girls so I didn't really mind this 'hazing' that i thought it was. After all this guy was both extremely hot and popular.

The next day was condom day in health and we all had been given 4 or 5 condoms on the way out the door. He saw me stuff them in the bag, so he came up pulled me away from my friends and whispered 'We'll put those into good use' into my ear.

This confused me even more but once again i thought he was joking and I didn't really mind it.

For the next week or so, every time i saw him he'd grab my ass and say something sexual in my ear. That was when it changed.

One day i was at school for a free block and headed into the bathroom to take a piss. Soon after dave came into the room, locking the door (it used to be a faculty bathroom so it was both nicer and smaller then the rest and also had a lock on the door) and then he checked the stall to make sure it was empty. Then he came up to me.

'Wanna give me a blowjob?' he said sounding serious.

'Ha-ha. No thanks, I'll pass' I said thinking he was testing me.

That was when he grabbed me, pushed me against the wall and kissed me. It was amazing an felt so right.

'How about now?' he said looking into my eyes with his beautiful face.

'What do you think?' I said still pressed against him as I began unbuckling his belt.

He smiled and kissed me. I crouched down and pulled of his jeans. I looked up at him and kissed him all the way up to his face and back down. I looked up at him, smiled and pulled down his boxers.

Out popped his fully erect cock and hit me in the chin. It was decent sized, but it the first one I'd seen that wasn't mine so it was beautiful.

'I know it's not huge.' he said looking down at me.

'Bigger then mine' I said not sure if that was true.

He put his hand on my head and I put his cock in my mouth. I sucked him until he came then i stood up and we kissed. The bell rang, he quickly put on his pants and as we left the room he quickly turned back 'don't tell anyone' he said nicely.

I saw him two days later in the commons making out with a girl, I instantly felt jealous until I realized that he had to keep up his womanizer reputation. He saw me and gave me a sexy wink that made me feel even less jealous.

It was a while before I saw him again but it was worth the wait, it was a saturday and all my brother's friends were over playing basketball. Dave was here to.

It was really hot and humid so I went to take a shower. Shortly after I got in I heard the door open. Thinking it was someone who didn't realize I was in there i shouted out 'I'm in here!'

There was no response so i looked out to see Dave standing there looking back at me.

'I have to hurry' he said throwing his clothes on the floor to reveal his dick and obviously newly trimmed pubes. I realized he must have noticed me getting annoyed at them while i gave him a blowjob.

He hopped in the shower and we kissed for a while letting our erect dicks rub into each other. We unlocked or lips and he grabbed my cock and I grabbed his. We stood groping and kissing a while then we stopped.

'Do you want to...?' he said pointing at my ass

'Not enough time' I said pulling him to the floor of the shower trying to hide that I was not ready yet for sex. We lied down and talked and groped for a few minutes.

'I have to go back they're gonna wonder what's taking me so long' He said sadly

'O.K. lets get out' I said. we turned of the water and got out. I rubbed him down with a towel making sure certain areas were especially dry.

He left the room and I left soon after.

A week later he left a note in my locker 'Motel, Friday, 9 pm, I'll pick you up' it read with a condom taped to it.

I was nervous and did not know wether to go. I finally decided that I would love to lose my virginity to this guy and decided to go. At nine on friday I saw his car outside.

'I'm going to a sleepover at John's house, see you tomorrow.' I said to my parents

'Wait, how are you getting there? do you have stuff you need?' My dad asked.

'Yeah I'm good John's brother is driving me' I said

'Ok, see you tomorrow.' my dad said as I rushed out the door. I ran out opened the door and got in Dave's car.

'Hey, lets go' I said to Dave leaning over to kiss him as we drove away.

'Where are we going?' I asked.

'My house.' he responded

'What? I thought we were going to a motel? What about your parents?' I asked

'We were' he said 'until my parents decided to go to my grandparents for the weekend'

'ok cool.'

We talked all the ride then finally got to the house.

'Ok its a surprise so put this blindfold on' he said handing me a tie

'Nice! I love surprises' I said putting the blindfold over my eyes. Dave led me to the his house into a room and told me to take the blindfold off. I took it off and looked around amazed. We were in the living room and he had cleared the couches to the side and put a giant mattress in the center of the room. On the mattress was a heart made out of condoms. There was a blazing fire in the fireplace and candles all around the room. I was so surprised i thought he was more of the play it rough types not the type to light candles!

'wow! How did you do this?' I asked

'I had time' he responded 'I have to go get ready I'll be back in a sec.'

He left the room. I quickly undressed and laid on the bed with nothing but a pillow blocking my crotch. When he came back in I cracked up. He had put whipped cream all over his groin so I couldn't see his cock and all over his nipples.

'Your going to have to clean it off before we can start' he said

'Oh alright I said getting up and licking some whipped cream from his penis causing it to instantly inflate causing much of the whipped cream to fall on the ground.

I first licked it off his nipple then proceeded to his dick. I licked off every bit giving him the occasional suck. He sat down on me on the bed his groin touching mine.

'Let me show you a trick I saw in a movie' I said. I put a condom in my mouth and rolled it with my mouth over his cock.

'Let me show you a trick' he said crouching over me and pushing me down. He put a condom on my dick and shoved his finger up my ass. It felt so good

'are you ready?' he said putting lube on his cock and on my asshole

'oh yeah' I responded heavily. He stuck his cock slowly up my ass. It hurt so much but it felt so good.

'its my first time' i yelled weakly

'my first time with a guy too' he said

We had sex all night and the next morning. And that was my first time.