Lessons
I was driving. Gray sat in the passenger seat. I don’t remember how we got on the topic. Probably one of my random non sequiturs.
“The thing is, I have this harness now. But. But. It makes me nervous. I don’t want to hurt anyone.”
“Don’t you have experience with a strap-on?”
“Just strap-on blow jobs. That’s different. Fun, but different. Less likely to be harmful.”
“What about at FetFest? Our threesome with NYRCherryBondage.”
“Yes, but that was fucking a vagina. Asses are more perilous.”
“Well, you won’t hurt anyone if you listen to them and follow their speed.”
“Yes. True. It’s just, to penetrate a guy. To have that control. And I’m not really toppy…”
“You of all people should know an act is not inherently dominant or submissive.”
“Yes. Yes. I know that. I know. It’s just. It makes me nervous.”
“Have you watched any videos on Kink Academy or PassionateU?”
“No,” I squeaked. He chided me for not taking advantage of resources I get for free.
“As long as you listen to the person, you’ll be fine. And just so that you know, yes, I am open to the idea of you pegging me, even though you danced around the subject.”
~
The first time I licked Gray’s asshole was in London, the morning I was heading home. The last time we fucked for months. I didn’t even know what I was doing. I licked and sucked on his balls. Licked his taint. Licked a little further. And then I heard the moan. It was different than he’d emitted before. And I knew what I’d done. I kept going.
“Show me how dirty a girl you can be.”
~
He stood in his leathers. I was on the floor, rope harness around me, my hands covered in soap and shoe grease.
As I worked on his chaps, I sunk down. Slithered in between his legs. My ass the last to drop down and through him.
I sat. Rested my back against his left leg. Tilted my head up. Massaged Black Gold into his leather as my tongue licked from his balls to his asshole.
He bent down slightly. Grabbed my hair. Maneuvered my face how he wanted it.
Later, when I finished his leathers, he asked, “Do you want to have some more fun upstairs?”
~
At Shibaricon, he sat on my face, ass pressing against my cheeks, as he fucked my tits til he came.
The night of my birthday, he sat on my face, ass riding my tongue, as he came in NYRCherryBondage’s mouth.
There is nothing so scary and so arousing as having someone fuck your face, not being able to breathe, and not knowing if they’ll remember to allow you air.
~
He laid on my bed, still in his leathers. His vest opened out. His chaps put his cock on display. His boots rested at the foot of the bed.
“You need gloves, lube, and dildos.”
I introduced him to my drawer full of safer sex supplies and masturbatory accoutrement. I laid the dildos by his side. Gloved up. Knelt at the end of the bed. Held the bottle of lube. Tried not to shake from nerves.
~
Now I remember how we got on the subject. It was the butt plug. The Mr. S Piggy butt plug.
I asked Gray for anal stimulation in our fucking. I wanted to get the plug in before next Fusion. I asked his opinion on masturbating with my introductory plug, smaller than the Mr. S prize. Any suggestions he had.
And then I mentioned the harness.
~
He had me lube my fingers. Lube his asshole.
“Too much is almost enough.”
He was specific; press, don’t poke. I remembered the tip from the two Kink Academy videos I’d watched earlier.
I pressed my middle finger against his asshole. I invited it to open. I pressed, and then felt the release. I slipped in, just a little. And then a little more.
Gray asked for more lube. I reapplied lube, then reapplied my finger. Glided in. My whole finger was in his asshole.
He wanted another. More lube. Again, slow pressure. And then two of my fingers were inside him. I felt his prostate; massaged it. Had his cock in my other hand; licked it. Inside, I reveled in the moment.
He grabbed my hair.
“Don’t you forget who is in charge right now.”
He let go of my mane.
He wanted to try a different lube. I slipped my fingers out; too quickly. I immediately knew I’d fucked up.
“I’m sorry.”
“It’s fine. Just remember, you go at the person’s pace. Grab the other lube.”
I did. We tried it. He liked it better, but I made a mental note to buy anal lube the next day.
I laid my ring finger across my middle and fore fingers; held the three together tightly. Pressed against his asshole. Heard and saw the pleasure I gave him as my digits slipped in. Again, I massaged his prostate.
His hands glided along his cock and rubbed his balls. His voice uttered his pleasure, until finally he said, “I’m cuming.”
I quickly readjusted. Put my mouth on his cock. Swallowed his cum. Played with his cock. Flicked my tongue along and around his head until he pushed me off.
“My only critique: I love it when I cum in your mouth, but next time don’t change up what you’re doing as I cum. Other than that, you were great. Now, turn around.”
He fucked me with one of my own dildos before we both passed out for the night.
Categorised as: Anal | Boots | D/s | Fucking | Gray | Leather | NYRCherryBondage | Rope | Sex
Comments are disabled on this post
Can’t wait to read what happens with a strap on when you do get the chance, sexy read
Wow. Loved this.
That was delicious to read – love following this journey!
xx Dee
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