Apr 062012
 

I normally suggest pegging him more often than we do it. I love to fuck him, I really do. But its his butt, and he doesn’t always want to have our big dildo up it. My boyfriend is kind of a size queen. We fuck with the Siren Dildo (see our review here)… its a girthy dildo. But that’s what he likes.

So last night, he’s wearing a hot pink thong. We’re playing video games, and I realize its already getting late. I tell him to pause, he needs a plug. Into the bedroom we went and he was giggling slightly. I pulled out the plug, rinsed it off in warm water, and covered it in lube. I turned around, and he was on the bed on all fours, ass in the air with legs spread. I spanked him for being so eager, he blushed a little but didn’t move.

I quickly but gently slid the plug in him. He gasped when it was its widest, and then sighed happily when it was all the way in. Back on went the panties, and he almost pranced back to his computer chair. Fast forward an hour or so, and he comes over to my desk, slightly tugging on the ring at the end of the plug. It was turning him on. I turned him around, moved the string of his thong away, and wiggled it. It He moaned. My bullet vibe was sitting on my desk, and I held it up to the plug turning it on a little bit. His eyes opened in surprise then closed in pleasure. I played with the vibrations more, and his dick started growing into its hardened form. I spanked him again, and sent him back to his desk.

Pink plug in his butt

Another hour or so, its very late. I tell him its time, I want to fuck him now. I ask him to try riding me. We’ve tried once before, but he hadn’t been plugged and it was too much to just sit down on to. I pulled on my harness with the dildo ready for him. I lubed it up and laid down, excited. He tried to insert it, but it was too big to just take in. We rearranged, him on his back, me kneeling in front of him.

I slid it into him gently. We looked into each other’s eyes as I slide into him, his legs curled over mine. Once in, I pushed slowly in. When I reached as far in as I could, he moaned in contentment. Yes, my size queen he is. I started to fuck him slowly. I got the angle wrong – and it slid out, the head making a sucking noise as it popped out of him. It hurt him a little, I repositioned and got the angle right this time, fucking him slowly. He was jacking off his dick, hard as I slid in and out of him. His legs began to curl up and I ran my hands softly up and down his legs. “Take my dick, oh good take it.” His eyes were open, focused on me as slowly fucked him. I was kneeling back on my feet slightly, watching my own hips move back and forth.

He had me swing my lips forward to sit on the bed. I did this carefully, making sure I didn’t remove my dildo from his ass. He sat up, moving his body toward me, we kissed with him sitting on my legs. It was close, intimate. He pushed my back and now I was lying down, and he was sitting on me in cowgirl, the dildo in him all the way. His feet were planted on the bed, and I pulled his arm toward me to adjust the angle.

He started bouncing lightly up and down, the look on his face one of surprise and delight. A brand new sensation of riding a dick. A minute passed and he was gripping the footboard helping him to balance. He admitted it was more tiring than he expected. I laughed, and told him to get on his knees rather than his feet. He readjusted, and now was grinding on me, dildo in his ass. I lubed up a hand and started jacking off his dick very slowly.

His face was furrowed in erotic concentration. He couldn’t keep his eyes open, they were closed in enjoyment. “Yes my slut,” I encouraged him. “Ride that dick, show me how much you like it.” He started to ride me faster, and I let his movements jack himself off in my now steady hand. He had to hold onto the bed to keep going, it was intense. He sat upright, supporting himself with his hands on my thighs as he rode . Moans escaped his mouth as he rode me.

He was lost in the moment, and I realized why he loves it when I ride him – what a beautiful site it is, your lover riding your dick, body moving freely, showing you all their pleasure for you to watch, to touch. You can see their whole body moving in pleasure on you. With you in them. My hand is still on his dick, jacking him off at a slow pace.

“You are so beautiful,” I quietly say, my awe of this beautiful site showing in my voice. He smiles shyly, and looks at me for the first time in minutes. “You are.” I say again. “So sexy on me like this.” He is overcome with emotion of the moment and the sensations, and he starts to cum, spurting his warm white cum on my hand and stomach. He spends the final moments grinding on the dildo, all in his ass, gripping the bed to stay upright.

When he gets up, his legs are shaky. Riding me was a lot harder and more physical than he expected, he had no idea it could be so much work. I laugh, loving that he can appreciate it when I tell him how I’m too tired to ride him at times.

We shower, and spend time kissing and hugging each other. I ask what he liked about being called beautiful, and I get more shy, cute smiles. He’s truly bashful, and won’t explain it. I comment that I wish I had a real dick, so I could better judge where I’m at in him. Having a dildo as your dick feels limiting, I’d rather feel it while I’m fucking him. The thought of me with a dick makes him bite his lip and almost shiver with excitement. He loves the idea, he can’t imagine how wonderful it would be.

  7 Responses to “Pegging in cowgirl”

  1. I knew a guy who was into hermaphrodites. Best of both worlds, huh? 😉

  2. We’ve never tried pegging and I don’t know if we ever will…but wow. That was beautiful and I “saw ” through your eyes what it might be like to have my love up above riding me.

  3. I just discovered your blog and absolutely love it. I cant wait to fully catch up on it. Its very refreshing and well written.

    Pegging is something I have been curious about but not sure how to go about it with a male partner. He would definitely love it if you were a shemale as it truly is the best of both worlds lol. I am a shemale fan and have some of my shemale experiences on my blog.

    • Thank you Dru! Happy to have you – I believe your blog is a recent discovery of mine, as well.

      I think when the time comes, if he’s open and you’re open, you’ll find a way to do it.

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