Sugar Baby Weekly

Monday, May 22, 2006

The Call

I looked at my phone and saw The Gentleman's name. He'd emailed me the day before, saying he wanted to ask my advice on something and he couldn't wait to talk to me.


"Hey, babe! How are you? Am I calling at a bad time?"

"Nope, what's on your mind?"

He went on to talk about how much he missed me, it had been too long since our last appointment. I agreed, and told him I was glad we'd be seeing each other The next day.

"Yeah, me, too. I guess it's not as hard for you to wait...I guess it's simpler for you, you know what i mean?"

Oh, great.

"I'm not sure what you mean."

In the next ten minutes he spoke and said nothing; how he has these feelings for me and inserting, 'oh, you know' at the end of every sentence fragment. He was not telling me everything and I was getting more and more impatient.

"Do you want to see me tomorrow?"

"God, yes! Of course I do!"

Another several minutes of saying nothing and I couldn't see the point of this conversation.

"Baby, I really need to go. Am I seeing you tomorrow?"

Then, like someone was holding a knife to his throat, he blurted,

"....I can't afford it!"

So there it was. Fucking twenty minutes on the phone and I now had a very big problem.

"You should have told me this at the beginning."

"I didn't want to hurt your feelings."

"This is not about feelings. This is a business arrangement. I am not your wife or girlfriend. You don't get to worry about hurting my feelings. You do need to worry about being disrespectful of my time. I understand that these things happen, income fluctuates, schedules get messed up, whatever. But I take our appointments seriously, and I don't think you do."

He was weak in his responses, self-pitying and truthfully, I wanted to punch him.

I ended the phone call, totally pissed and really worried about how I'd pay my bills.

Anybody know any nice, respectful, dependable guys?

Friday, May 05, 2006


He walked over to me and pulled me up so I was standing in front of him. I was in a bad mood. I was really anxious about my finances because things weren’t going so well at my job, and while I usually look forward to our meetings, the only reason I was there on that day was that I needed the money.

That’s not a good feeling, by the way.

I guess if I had a better whore persona I’d have known how to mask my surliness without seeming fake. I’m not sure how that works; I am not very good at pretending to be enthusiastic about something when I’m really not. I figured the best thing to do was just to tell The Gentleman that I was having an off day.

“I’m sorry, baby,” I began, “but I’m just not feeling very sexy.”

“Cara, you look so great…you’re incredibly sexy.”

“Thank you, I'm just in a funky mood.”

“What’s troubling you?”

“I really don’t want to talk about it; it’s just stuff. I was looking forward to seeing you, and now I can’t get this other stuff out of my mind. Maybe I can give you a backrub?”

“Why don’t you let me give you a massage,” he said.


“I’d love it. Let me help you undress.”

I laid down across the bed and he sat next to me and massaged my back and shoulders. It felt nice, and I closed my eyes. I didn’t want to talk. Soon his hands were on my ass, massaging and sneaking down between my legs and forward to my pussy. I think he’s maybe got some short term memory issues because every time he fingers my pussy I wind up reminding him where my clitoris is and that making little circles at the lower point of my vaginal opening is not very pleasant. It’s actually pretty annoying.

Once I guided his fingers to the right spot I tried to get into it, knowing that if I came I would feel so much better about everything, but my body was not having any of that. After a while I raised my hips and rolled onto my side, signaling for him to stop. I took his hand, saying, “I’m sorry, I just don’t think it’s happening right now. I need a break.”

He laid down on the bed next to me and we talked. There were basketball games on the TV, but the sound was off.

“Cara, is there…”


“Oh, nothing.”


“I was just wondering if there’s anyone you’re interested in being with, like, a boyfriend.”

Oh, fuck. This again. No way am I telling him about my personal life. It doesn’t matter and he shouldn’t ask. Ours is a business relationship, ideally free of those kinds of concerns. Why doesn’t he understand that? Why can’t he respect that?

“We don’t have that conversation, remember? It’s counterproductive to our purpose.”

“I know, I know, I just keep thinking that you should have a boyfriend since you’re so young, but you’re also probably too busy to have one, aren’t you?”

Again with the personal assumptions. I have to say I’ve gotten pretty good at circumnavigating the questions in my responses,

“My life is just the way I like it.”

“Do you want to suck my cock?”

“No. Hand me the lube.”

He gave me the bottle of Pink lubricant he’d bought for me a few weeks earlier. I squirted a couple times into my hand. His cock was hard; he’d been touching himself as we talked.

By this time, I know just how to stroke The Gentleman’s cock, I’ve watched him do it so often. I make a tight tube with my hand and use my thumb to spread his precum over the head, sliding down the shaft. The stroking is with the flats of my fingers and thumb in an up and down and slightly circular motion.

I don’t think he’s ever jerked off using lube, because he is going crazy about how good it feels and I’m just sort of mesmerized by the sight of his dick throbbing under my fingers. When his breath gets quick and his cock seizes and he’s about to blow I close my fist around it and stroke just the tip with my thumb and forefinger, milking it.

He shoots, which is unusual. He’s a dribbler, not a shooter.

(I just impressed myself with NBA Playoff metaphors.)

Anyway, the thing is that it may not have been the smartest thing to let myself be vulnerable with him during our appointment, but it felt better than putting on an act that everything was just great, he was so hot and my mouth couldn't wait to have a big helping of his cock.

I guess that's the drawback of regular clients for escorts. Most of the time it's nice because you know what to expect and you become comfortable together sexually. You even come to care about each other in a certain way. You just need to be able to stay within the boundaries of your defined relationship.