Prostate Milking While Pegging My Boyfriend

September 25, 2023

My boyfriend’s pegging kink turned into prostate milking.

Prostate milking was the next fun little search in my boyfriend’s porn history. Once I fucked his ass with my toys, he wondered why it felt so GOOD! And his curiosity led him somewhere even kinkier. He had recently been searching for pegging porn all the time and that’s when I first found out his dirty little secret. All the time we’d been together, he’d wanted to be my little slut instead. So, I finally gave him exactly what he wanted. That night I first pegged him, he was insatiable. He was so excited for the foreplay. The feel of my wet little tongue rimming his ass, the feeling of my fingers sliding in and lightly pressing his prostate. All of it was a whirlwind of ecstasy to him.

And that feeling stuck with him; he was so horny to try it again! All week long, we cracked little jokes about it… but I didn’t know what he was really asking for until I saw his porn history. He had been such a naughty boy. He had even been searching for how to milk his own prostate! That’s when I cracked a mischievous little idea — I was going to buy a vibrating toy and show him the next wonder of the world. He’d already experienced my tongue, fingers, and strap-on. Now, we were on to the next adventure. So I went shopping for toys I could use for prostate milking. I knew his favorite was going to be a curved vibrator. It was almost as thick as the strap-on I used to peg him, but it curved nicely so that it would hit his G-spot every time.

He was going to love all these new sex toys.

As soon as I got home, I cleaned them thoroughly and hid them away. I teased him all day about how we were going to do it all again. We sexted for hours as I taunted him about how I’d make him cum more than he ever had before. He was so giddy when he got home! I made him hop in the shower and then wait for me on the bed, naked and excited. “You know how I want you, baby. Lay back for me.” As I neared the bed, I made him put his legs up. First, I stroked his cock just a little bit as I unveiled my big plan. “I found all that prostate milking porn you were watching…I thought we should try it.” As soon as I said that, he presented his ass to me, craving it immediately.

I giggled and moved over to the bedside table, taking out his new bag of toys. The show-and-tell part was so much fun to me. He laid back, curiously watching as I demo’d the first toy on him. It was a little, curved, pink vibrator that I generously coated in some lube. And at first, I teased just his cock with it. Bzzzz. His eyes shut as I worked the vibrator down the length of his cock, teasing nad massaging his balls… And then I applied a little more lube, and he felt that warm, wet, juicy pleasure rubbing against his tight little asshole. He couldn’t help but moan, daydreaming about the prostate milking that was yet to come. I slid the toy in just a little, really letting him feel it.

The vibrations were almost enough for prostate milking already!

I slipped the toy in a little further, using the curve to press the head up against him, angled towards his balls. As I slid it further in, he let out a gasp. Jackpot. I pumped that toy in and out of him so gently, letting the curved head rub against that same spot. A little pressure, a little variation in the vibrations… He was so excited he was gripping the sheets and practically humping the air. “I know, baby, I know…” I giggled as I pressed the toy against his G-spot even further. Oh, the pleasure of that prostate milking was driving him over the edge. His cock was dripping with pre-cum. And then I swapped toys! The next one I unveiled was a string of vibrating anal beads. At this point, he was so horny he even spread his cheeks for me to slide them in.

Oh, the toys we will discover together… Maybe next time, I’ll even try using one of those wifi/Bluetooth connected toys so that I can play with the vibration levels as I make him ride it. It’ll be so fucking hot to see how hard he cums from that!