I wanted his first anal experience to be as romantic and as erotic as mine was. Sissy Twinks are delicate so I had to do it right. Checked into the hotel that caters to couples like us. Clothes off, wine poured. He was a little scared, limp cock shiny waxed balls, held my cock, said that's a lot bigger than your finger, daddy, will it hurt? No son, just feel a little pressure first. Now give it a squeeze and I'll lube you up. I took him out onto the balcony to admire the pool/Jacuzzi clothing optional scene, edging, oral. That got him hard and eager. I spread his legs, elbows on the railing. He gave short high pitched scream when I forced my cock head past his rim. After that he moaned, backed down on me and begged me to go faster. I did because that cute little ass needed seed balls deep. A couple of men and a boi waved at us. After I came, told him squeeze hard, suck my shaft dry when I pull it out. Turn him to everyone down there could see me take his pretty cock in my mouth. About 20 seconds later I had a mouth full of cream, his fingers digging into my hair. After a walk down to the pool and Jacuzzi, chit chat, maybe find him a boyfriend, I did him again doggy style in the privacy of our room, just him and me, worked him a long time before planting my seed, the I sat on him and showed by example how you work the rim and inner muscles to maximize cock head and shaft friction. We were up late and slept in. Didn't find him a boyfriend, but I got a dose of man cock and man cum from a guy down the hall.

Deep, tears running down his cheeks, eyes up at me.

Wise men let their cock decide. Good thing I douche before every intimate or casual encounter (force of habit and feels good too). Men our age, it's mostly oral pleasures, but when he popped his magic pill while I poured us drinks and began fondling my ass, have to admit I got a little excited. Couldn't get down on my knees and elbows fast enough. His meat is longer and fatter than average. Nice thing about mature sex is we take our time. Took a few breaks to refill our glasses, a little stroke and oral. Over an hour later he started the jackhammer, the final pumps in rhythm with "You. Fucking. Whore."

He's right about that, and it's the best massage I've received in quite some time. Thank you, Carl. Love, Jonathan

I gave him his first blow job for his 19th birthday, gave him my cock and cum in the two ways that matter most.

That tiny twink's 2 inch tiny cock pumped out a massive load. Swallowed half of it, dropped the rest of the snowball into my margarita and sipped it while helping him learn how to suck cock in a quality way. Lips work the shaft, tongue works the head, son. His sweet little tight ass didn't need any mentoring. Once I got my head in the shaft went balls deep without difficulty. Moaning, whimpering, just a little pressure, seed planted.

I prefer sex with mature men, but I feel obligated to cultivate fresh talent.

In the mood for thick man cum. I'm complicated, lol.

I rarely do that. Took the ruler out of my kit I use for teacher punishing students who disobey role play. Rock hard, 1.6 inches. Pumps out a very large snowball for daddy. Shallow throat, tight ass. Kept him for the weekend. His boyfriend understands. Do him later.

He sat on my lap, put his head on my shoulder and said, "Uncle Jon, all I want for my 21st birthday is to drink wine, suck cock and eat cum." Talked to his daddy, arranged for a dozen men to give him the birthday he wanted. We all came twice, 21 swallows, a few came three times (the anal seed kickers, lol). Pretty cool.

His comment. I gave him my cock and my cum, a loving daddy to a twink who needs to be loved. Late bloomer, 21 y/o virgin. Told him, son, the safest sex is masturbating to porn. Good job!

I'll pop his virgin cunt next weekend, doggy style of course, plant my seed balls deep. He's excited and a little scared. It wont hurt, you'll just feel a little pressure when I force my cock head inside you. A few pumps and you'll be backing down my shaft.

I filmed him getting his first blow job from me(you are welcome, X-tube). He's shy, but I'll have the camera ready just in case

That pretty much sums and cums it up. Enjoy your holiday everyone!

He got off watching me fuck his bitch, I got off fucking his bitch, the bitch got off being fucked. After he ate our cum we shared his cream. Sort of like a 3-way, lol