Something So Familiar

A couple of weeks ago I received an email from Viviane of The Sex Carnival asking whether she should add my blog to her list of the dearly departed sex bloggers. "No!" I practically screamed at my Gmail.

Her point, and that of several of you, dear readers, was well taken: it's been way long since I spent quality time, just me and my keyboard, pinging out the stuff that feeds your imaginations and dammit, makes me smile to read it over again. I could tell you that things have been busy at work (they have), or that I went to St. Moritz over the holidays (I did not, but I could tell you that), but the truth is that I've been very lazy and more than a little bit conflicted.

Lazy because, well, it's easier to stay in the habit of not writing than it is to forge a whole (almost) new one of writing more regularly.

Conflicted because I had this dream.

It was a couple of months ago, after a business trip with The CEO where we spent 42 hours together, about four of them sleeping. We went shopping, ordered room service in our swanky hotel, walked on busy streets in broad daylight and ducked into a bistro for lunch. That was the trip where he referred to himself in the third person as my boyfriend and it caught me off guard.

So, in the relevant part of my dream he and I are in his car and we go to pick up his two sons. I move to the back seat and start having a conversation with one of them. Then the CEO stops and runs into a shop to pick up something. Basically, I am tagging along for errand-running. The boys have some kind of practice, and he's dropping me off at my house. He pulls up, gives me a quick kiss, and as I am opening the door and stepping my foot onto the pavement I say, "'Kay, byeloveyou."

I know. I KNOW.

And as soon as she said it, the dream me clamped her hand over her mouth and omigodded.

Then of course, I woke up. Then of course, I freaked out. Am I seriously in love with The CEO? I mean, it would be alright to be in love with him if A) he wasn't married, and B) didn't pay me. That's WHY you look for a girl friday--or wednesday, as is often the case--to avoid emotional entanglements. And here I was getting emotionally involved.

Alright, so now I'm emotionally involved.

I told my friend who used to escort what happened, and I tried to think about what it really was that made me say such horrible things in my subconscious. It was, after all, a dream, and not necessarily meant to be understood literally. I decided that I'd explain it to myself as a natural progression of things; as in, I'm increasingly comfortable in his presence, and isn't that what people who are comfortable with each other do? Isn't that what people with a certain familiarity say to one another?

It's what I say to my friends when we hang up the phone or say goodbye on a street corner. Quick cheek kiss, hug, "loveyoubye!"

For about a week I was conscious of how many times The CEO and I spoke. I made myself let his calls go to voice mail and returned them later. I focused on my job and my friends and not on how much I would miss seeing him when he took his family to Australia over Christmas.

I didn't tell him about the dream. And apart from those ten days last month, we've seen each other for sex and familiarity every week, once a week. Sometimes twice.

Dressing Up

Have I mentioned how I love dressing up?

I think I have, but for those of you new to the blog, let me be clear: I really enjoy dressing for sessions. It's my little ritual, which we all have, like for dates and stuff. And of course you want to wear something on a date that your boyfriend will like, but you don't (at least I don't) ask him what he wants you to wear.

Girls also dress for other girls. We're constantly checking each other out at the supermarket and the swimming pool (I was at my pool the other day and this searingly hot Amazonian fox was wearing a bikini top and these really weird coordinating shorts, i assumed to cover her ass. I was incredulous. She totally should not hide her ass. Of course I didn't say anything. Of course I digress.)

I dress for the CEO the way I know he likes. I asked him what he'd like me to wear for his commencement speech.

"Dress like you're a recruiter for a big hi-tech company."

"Like, what, a suit?"

"No need. Dressy business wear. It's summer."

Excellent.

So I got dressed that morning, after painting my toenails a nude shade of pink. I checked the mirror one last time before heading out: my white blouse with the semi-seethrough swirls in the fabric, nude colored bra underneath, a black pencil skirt with a flare at the knees, and black strappy heels. I had my red briefcase filled with condoms, lube, a vibrator and my laptop.

He was nervous when he walked into the hotel room. I took his bag and kissed him hello. His assistant had messed something up at work and he was flustered and annoyed and needed to leave the office to fix it. And now he was here with me. I lowered my voice about an octave and spoke quietly. It works with my cats. I undressed him and kissed his mouth to shut off the rambling.

His eyes were closed and he had that little smile he gets when he's relaxing, just like my cats.

It was at that point that I realized, really, what my role is for the CEO. I am the calming influence. I leaned into his ear, "Hey, Mister, watch this."

I slid down to my knees, wearing all my clothes, putting my hands on his hips and looking up at him from underneath his hard-on. "You look like the hottest recruiter ever," he said. "Sit on the bed," I said, "and pretend it's your office chair." I smoothed my hair and smiled.

I blew him on the edge of the bed and cleaned him with a warm washcloth. He said he wanted to kiss me all over. I stood up and undressed, not being showy, but definitely being deliberate. He smiled and pulled me over. He nuzzled my stomach and licked my belly button. He sucked my nipples. He turned me onto my belly and laid on top of me with his arms under the front of my shoulders. He spooned me from behind. We didn't fuck.

We showered and I brushed powder on my face as I watched him get dressed. He left ten minutes before me. When I grabbed my briefcase I saw the stack of bills in the small compartment: three times my hourly rate. Of course, we weren't finished, I was going to watch his speech and look hot from the audience. I put on the glasses he likes and looked down at my feet, "I should make sure I sit at the end of an aisle. When he sees me, my legs will be crossed and a foot dangling in the aisle."

Synchronassity

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.

Mister

So, I've taken to calling The CEO "Mister."

To his face. Like Claire Danes' character in the movie (and book–the book is really good! And Steve Martin wrote it, the fancypants.) Shopgirl. It's funny, because it started off in my head as "Mister Big," which I would never have called him to his face. But tell a girl about your cars to the airport and private planes to The Bahamas enough, and she'll come up with a suitable pseudonym for you. Soon, "Mister" worked its way into my greetings to him.

As in, "Hi, there, Mister!" Or, "Hey Mister, roll over so I can put my mouth on your cock." Stuff like that.

Following suit, he started calling me Miss.

It adds to the discreetness and covertness of our relationship, and it's not icky Dominant/submissive like it would be if I called him Sir. Which I would never do. Because, eeyew.

One day we were lying in bed at a hotel near his golf course while he was supposedly playing the back nine, when he asked what I was doing the following week, "Um, seeing you?" I replied.

"I hope so, but get this: The Business School at XYZ University has asked me to speak at their Commencement that day."

"Wow, Mister, that's special!"

"Yeah, but I suck at public speaking."

"Would it help you relax if you were sucked before speaking in public?"

(A-hahahaha. I crack myself up.)

"Miss, you read my mind. That could be just the thing to take a fellow's mind off of speeches. I'd like you to come to the thing, too, if you could."

"Wouldn't it make you nervous if I was there?"

"No, I think I'd feel better knowing you were out there. We could meet here and then drive over separately and come back to the room if there's time. So, yeah, I'm talking about all afternoon."

Oh, the prospect of this got my knickers wet.