I'm 28 and this is how I imagine my first time to happen with an older man, maybe late 50's.

'Hi! Nice to meet you." I said.

'Finally! Nice to finally meet you. You are one sexy boy in person! Come in. Can I get you a drink?' You reply.

'Definitely. Beer please, anything cold. Make it two!' I nervously laugh.

He showed me around this apartment quickly, all looked very neat and tidy. Then we sat down at the table where he had prepared some of his 'gourmet' snacks he's always talking about.

We did the usual idle chit-chat as I nearly chugged my beer.

'So Jim,' he said, 'What do you want to get out of this?'

'Well,' I said, 'If you could be prepared for everything, but expect nothing, that would be a good place to start. But I'd like you to push this process along. Don't wait for me to make any moves. You know, sexually. Be a little pushy and agressive or else we'll end up talking all night.'

He laughed and nodded his head. 'I think I understand. Nothing to worry about.'

'We can maybe start with an all male movie, then possible a massage, just like we always talked about. If things go well, maybe bring out some toys, you know, to loosen me up? If you like, you could shave me 'in there' and help me get clean. Oh, I'd like you to use a condom too. Maybe after a few times, we can get tested just to be safe, then we can really get into it.'

'That would probably be a good idea. The cleaner the better. What do you say we move to the family room and get that movie going,' you said.

'Sit there,' you point to the middle cushion on the couch and fiddle with the DVD player. 'I hate pornos with plot. Let's fast forward eh?'

Soon enough, the two men in the movie are naked and one is getting sucked.

'What do you think?' you ask.

'Well I can hear my heart pounding in my ears, but it's good.'

'Good. Now I want you to stand up and take your clothes off. Slowly too.'

I took a second to comprehend what you said, when you sternly told me to hurry up. Like a good boy, I did. I began with my shirt and dropped my shorts, standing there in my underwear.

'What are you waiting for? I want you naked.'

I dropped them to reveal my semi-erection. 'Excellent. Now, turn around and bend over. I'd like to see the goods if you don't mind.'

I did just that and felt your hands on my butt cheeks for the first time. Just that touch gave me goose bumps. 'Looks like I've got my work cut out for me. Lets go into the bathroom and get you fixed up. Is that okay?'

'Sure. What ever you think is necessary,' I replied.

In a flash we were in the bathroom and your hand was full of shaving cream and you were spreading it on the crack of my ass. 'If you're comfortable, I can shave it. It's hard to do yourself and I promise I'll be as careful as I can,' you said.

Once that was done, you brought out an enema kit. 'Do you want me to help you with this?'

'No, I think I can handle that. I've done it once before,' I replied.

'Okay, I'll be watching the movie when you're done.'

I finished my cleaning and walked back to the living room to find you naked and playing with yourself. In the movie, the smaller man was getting a good hard, raw fucking. I sat down next to you and you immediately grabbed my cock. That was the first time anyone has ever done that, but there will be many more first times tonight.

After a short while, you stood up and grabbed my hand and led me to your bed room. I noticed on the night stand were two dildos, a vibrator, box of condoms and some lube.

'Lay down on your stomach and I'll start your massage,' you instructed. 'Just relax. You can say no at any point and I'll respect that no matter where we are at.'

I did as he asked. I then felt the cool massage oil drizzled down my back and a few drops into my freshly shaved ass. The massage felt really good. I particularily liked when you massaged my neck because when you leaned forward, I could feel your semi-hard cock pressing into my ass crack.

As your hands went down, I felt your fingers caress the insides of my ass cheeks. I was feeling comfortable so I opened my legs a little and without hesitation, I felt your finger touching my hole.

I took a deep breath as you pushed it in. 'Okay?' you asked. I nodded.

Then I felt another. 'Still okay?'

'Yeah.'

'Good. Just let me know when to stop but I'll just keep going if I don't hear any objections.'

There was something soothing about your actions. I was incredibly nervous but I just knew this would be okay. You were really massaging my muscles in the area and it felt great.

'I think you're ready for something more,' you said. With that, you jumped off the bed and brought over the dildos and vibrators. 'Little one first, obviously.'

Slowly you worked it in and paused, then withdrew it and pushed it back in a few more times. To my embarrassment and amazement, I suddenly came! I tried to hide it but I bucked wildly and moaned. I had an erection since I laid down but I didn't think I would cum so fast.

'Oh! I see someone likes it,' you said as you reached underneath me and pulled out a handful of my cum. 'Next one.' You wipe my cum on my back.

This one went in well too but I could tell it was bigger and you did the same routine: in, pause, out, repeat.

'You're doing very well. This one inside you now is only a little smaller than my cock. I think you're going to be a great slut for daddy. You want to be daddy's little cum holder?' you asked with a grin.

Your change in tone surprised me a little but excited me even more.

Then I felt your cock pressing on my ass, and it was beginning to stretch to take it. Much slower than the two dildos but I was adjusting.

A little uncomfortable but I knew I would get used to it. Just then, I felt it 'pop' and I knew you were in. You paused, grabbed my wrists above my head and began to pull it out.

Paused again. And pushed it back in.

'How do you like that?' you asked.

'It's good. Keep going but slow. Please,' I replied.

'Don't worry son. I want you to come back and beg me for more so I won't do anything to hurt you.' With that, the discomfort went away and I pushed back a little.

You let out a little groan and began to pump at my tight, virgin boy-pussy. I reached back and touched the base of your cock which was at the opening of my ass. I couldn't believe it. I finally did it, and I've done it with such a huge cock!

Soon enough you were fully fucking me doggy style. Suddenly you stop, flip me to my back and lift my legs.

'Now you can watch me fuck you a little better. Are you still okay?'

Before I could answer, your cock slid right back into me and I could see it going in and out just a little as I sat up. This lasted for a while until you stopped, laid down and told me to sit on your cock.

As usual, I did as I was told. As I bounced on your cock, you grabbed mine and began to pull. It wasn't long before I was moaning loadly and before I knew it, I came again. This time all over your chest!

You smiled and kept right on going. After a few more minutes we switched back to doggy style and you really started humping and fucking and I could feel your cock twitching. You moaned loudly and came.

We collapse, with you still on, and in me.

In complete shock and lust at what I've just done, I can only imagine where this relationship will go. Vacations at the cottage, maybe more exotic, no condoms, pure sexual freedom and you'll continue to be my sex teacher, master, father, whatever.