Sugar Baby Weekly

Saturday, August 04, 2007


The week before The CEO's commencement speech we met as usual. I checked into the hotel, he showed up in sweaty golf clothes thirty minutes later. This time, he was sweatier than usual and I was all over him. I like sweat–clean sweat–on a guy who's recently showered. I was keen to show my appreciation for his salty-slick skin, turning cold from the air conditioning, which as it turns out, had no effect on the state of his cock.

I whispered how hot it made me to taste his sweat and his cock surged even harder against my belly as I stood on my tippy-toes to reach his neck. He walked me backwards onto the bed and I scooted back, propping myself up on my elbows as he followed me on his knees. He fed me his cock and all that, and then he kept moving forward, inch by inch.

At a point, I thought, "does he want me to lick his ass?" And then, "OMG, he totally wants me to lick his ass!)

Ah-hah! The CEO likes it when girls play with his bum! How happy did this make me? Very happy, indeed.

Believe me, I'm perfectly glad to give the man an hour-long blowjob, if that's what he's paying me for, but if the possibility of a little kink presents itself, I am thoroughly pleased. It keeps my job interesting, and opens the gates for more satisfying encounters. The CEO is married, and–not that it applies to all marriages, though it's becoming clear that it's not an uncommon thing in married men–not getting any at home.

We don't talk about it, his marriage, but things slip out now and then, and from our first meeting he's been remarking on how many "first-times" he's had since then. I was the first girl he'd ever jerked off for, the first he'd watched jerk off, who'd let him come on her tits, the first to suck his cock on her hands and knees while he kneeled on the bed and got a stellar view of raised ass. I was game to chalk off a first for every time we met, but my brain was starting to quaver, trying to come up with new positions and configurations. Now it seemed I had more material to work with.

The sounds from above me as I toyed with his ass with my finger while my tongue sucked on his balls were fantastic. He was kneeling above me on the bed, bracing himself against the wall and his legs were shaking from the effort. I suggested we change positions.

"Do you like it when I play with your ass?" I asked, grinning.

"Yeah, I really, really do," he said.

"Good, because I really, really like doing it."

Unfortunately, I hadn't brought any ass toys, since this was a new revelation and I was late leaving the house. Live and learn, I thought. Not to worry, I still had gloves and lube, and that was going to have to suffice. I put him on his belly, ass up, and stuck a glove on my left hand. I pulled the condom off his cock, lubed my glove, his ass and my other hand, and started to stroke his semi-erect dick.

He likes it fast and shallow at first, concentrating on the head, and then moving into a steady and firm full stroke. I watched him jerk off on our first meeting. I blow him regularly and take extensive mental notes. Once he was hard and starting to circle his hips with my handjob, I took my other hand and again started swirling around his hole with the tip of a finger. Swirls became circles, became more insistent pressing and rubbing with my ring finger.

"Relax, Mister," I whispered, "take a deep breath and blow it out."

He did, and my finger slipped in. He took it completely, and I could tell he was smiling.

"How does it feel?"

"It's like my brain's on overload. It's so good, please don't stop."

I felt very protective of my CEO, like a mother who covers her babies with her body to keep them from harm, like that lady vampire in Interview who tries to shield Kirsten Dunst from the sunrise. It's true, my heart melted a little and I leaned over him, brushing my tits against his ribcage, bending forward and talking low, "I'll stop when you say, but I like this very much."

I kissed and bit his asscheek softly.

He inhaled as my grip tightened on his cock. I stroked it steadily, making sure my thumb circled the head on the upstroke the way he likes. Then on the downstroke I started pumping my finger into his ass like a goddamned piston firing. Both hands working toward one another, one firmly jerking his cock, the other gingerly fucking his butt.

The CEO likes to have permission to come. When I first started seeing him, he'd say, "A dude could come at any time if someone would say it's okay." I thought that was a little odd, but charming in a way, and I'd say, "You know, Mister, I would really like for you to come now," and he would. These days, I know when he's about to blow, and I'll just say something along those lines.

His dick was solid hard, his balls pulled up, the man needed to blow, "Hey, Mister," I cooed, "you know what would be really hot? You come on my hand and I rub it on my tits."

He moaned, his breathing was shallow, and the tell-tale "ah yeah, ah yeah" was happening up in the pillow. Then something not that unusual: his dick got soft, his ass tensed up and he grunted into the pillow.

"I can't."

"Okay, hold still and take a deep breath."

I retracted my finger and snapped the glove off inside-out. "You okay?"

"Uh-huh. I was so close, I don't know what happened."

"You froze up a little bit when I started massaging your prostate."

"That's what that was? I felt like I was going to die!"

"Baby," I kissed him, "you would have died a very happy man."

"Can we do that again?"

"Bet on it! Next time just let go and relax when you start to feel like you're going to die. I promise It'll be amazing."

"Miss, when you were licking my balls I thought, 'Oh, my god, is she going to lick my ass? I think she's totally going to lick my ass!"

Hah! Now that's some synchronicity.

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  • At 12:15 AM, Blogger dusio said…

    that may have been the single hottest story I've read in ages.
    Wow. I so envy your CEO.
    oh my my my.........


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