Sugar Baby Weekly

Saturday, April 28, 2007


I started thinking that maybe I should just hang up the whoring shoes.

The Gentleman had checked out, with my blessing and encouragement (he's really not cut out for this kind of relationship emotionally, not to mention financially). I hoped I'd been a fun distraction, that maybe he'd learned a little about how to ask for what he wants, and had gained an appreciation for his partner. He still contacts me occasionally, and I steer clear. Simply, he cannot afford me and I'm not going to reassure him that, no, I don't think he's a terrible person, blah blah blah.

After The Gentleman, there was a string of several forgettable men, none of whom excited me, and a couple of whom really pissed me off. Disrespectful, presumptuous, stupid and rude, these were definitely not people worth my time and effort: No, my fee does not include the cost of the hotel room. No, we can't forget about the condom. No, the fact that you're paying me doesn't mean you get to do whatever you want.

Hmm, apparently I haven't totally forgotten them.

While I liked the money, I was not so hard up for cash that I had no other options. I started thinking about what I liked best about my relationship with The Gentleman. I realized that I was filling a void for him, and that I was fulfilling a fantasy. I was helping him socially, not just putting on strip shows and tying him up. He thought I was wonderful, and he told me so every time we met.

In my meetings with these potential candidates, aware that they were judging me as much as (actually, more than) I was judging them, I concluded that I was having precious little fun and that this was beginning to feel like work, which meant it was time to take a break. So I did.

Until last week.

I was apartment searching on my city's Craigslist when the temptation struck. I went to look at the Personals, just to see what was there. The usual any girls want to get licked? and i got what u need- u must host- tonight only! were passed over. For real, dudes, the honor of a click from my selective thumb is given to those posts containing the words "businessman," "generous," or "discreet;" preferably all three, with discreet spelled -EET, not -ETE.

As if by magic, Generous Businessman Seeks Discreet Daytime Encounters called out to me like a siren, taunting my index finger into tracing indecisive circles on my trackpad. What the hell. I clicked, responded and within 12 hours was exchanging emails with someone engaging and clever. His email contained his first and last names, which I Googled. He was, indeed, the CEO of a successful company. Early 40s, pleasant-looking from what I could tell (of course I did an image search), and involved in several local charities.

Our conversations were easy and respectful. No "so how much do you charge and what do I get for that?"; no "can you come to my office parking lot so i can suck on your toes?" In fact, nakedness wasn't even mentioned except circuitously, and I liked that. We arranged to meet for an hour. His travel schedule was insanely full, and his assistant managed his calendar. He had a window today at 1:30.

He was tall, taller than his photo suggested, at well over six feet, and very good looking. We sat together and chatted about music and art and sports. He smiled at me and said, "You're such a delight!"

"I hope to be," I said.

Within minutes we were naked. He had described himself in his ad as very fit, and I couldn't argue. He was lean, not overly muscular, and his head was bald on top and shaved on the sides.

He was, in my estimation, hott.

He'd appointed me keeper of the clock and unfortunately time was not on our side. I suggested a massage for his back and glutes, which must have been tight from all that triathalon training he was doing. omg totally awesome bodyyyy Um.

The massage didn't last long. My curiosity got the better of me and I slipped my hand past his well-formed ass, down between his legs, which he parted, lifting his hips slightly. My other hand reached around front and wrapped around his Very Hard Cock.

I hummed my approval at this (not-such-a) surprise, and suggested he turn over. He did, and stretched his arms over his head, affording me a rather nice view of him from stem to stern. His ankles were off the end of the bed. Damn, but he was tall.

After several minutes of continuing our conversation (what was it about, again?) as I played with his dick and balls and sat next to him on the bed, I leaned back, mid-sentence and stuck a condom in my teeth.

He stopped talking, mouth agape, and watched me position myself between his legs, my right hand holding his cock like I was some kind of fighter pilot. I set the condom on his head, balancing it like a jaunty little tam, smiled up at him, and rolled down his shaft with my lips.

I thoroughly enjoyed blowing him, hearing his voice when I took him down my throat and moved my head front and back slightly--quickly--until he sucked his breath and raised his hips up and came quietly.

"Very nice!" I commended.

"Uhh, easily the best I've ever had," he said.


He laughed, "Um, YEAH. You're awesome!"

After ten minutes of making out and him licking and sucking my nipples, he was hard again. Wheee! When I commented on his hard-on, he said something like, "I don't mean to sound conceited, but yeah, I'm a good dude." That cracked me up. I couldn't believe I was having so much fun.

I suggested he let me watch him jerk off, which he was a little hesitant about. He's never done that for anyone, but "If you think it's hot, I think it's hot." I assured him that I thought it was very hot, and that I'd assist him if he wanted.

"Would you like some lube?"

"Uh, sure..."

He was propped up on one elbow and stroking his cock, which he held pointed up for me. He was probably expecting a squirt from the bottle, but I had something else in mind. It's way hotter for a girl to spit on your cock, right? After I dropped my shiny spit onto his knob to, in my mind, a chorus of "awwww, yeah"s, I slid behind him and wrapped my arms and legs around his back, supporting his body and resting my chin on his shoulder while telling him how hot watching him made me.

The thing is, it really did.

When he was close to cumming, I took over, jerking his dick and pinching his nipple as he arched his back into me and shot again. Um.

"Wow! You ARE a good dude!"

He had to leave, so we rinsed and dressed. I was running a comb through my hair when he came over and said, "I am so glad we met. I even came prepared in case I really liked you," putting something into my pocket.

"Oh, thank you! I had a great time...I'm glad we met, too!"

"I'm out of town for a week, but I absolutely want to get together again soon."

"I would like that very much. Definitely."

I let him leave first and waited a few minutes. I really had fun, really liked this guy. Maybe it's bad whore form to feel charitable toward someone who's paying me to get his rocks off, but I look at it as an added bonus. I get to make money and have a great time; what's wrong with that? If I were working for an agency, I'd have a totally different set of random, anonymous experiences. I'm not interested in that kind of whoring.

I was in a very "thank god--finally, someone who I like and who appreciates me and is totally cool with giving me money" kind of mood. I took the folded bills from my pocket, blinked, and looked at the clock. It had been 50 minutes since we met and he'd already paid me for an hour.

The CEO had given me a $150.00 tip.


  • At 4:46 PM, Blogger Viviane said…

    Awwww, yeah!

  • At 1:24 PM, Blogger LA Player said…

    So another CL success story. And to be successful, how much?

    Often I do wonder, after I leave, will the girl look at the tips and say, "am I a waitress? you silly".

  • At 8:13 PM, Anonymous Anonymous said…

    oh please post more - i have missed you so!



Post a Comment

<< Home