Sugar Baby Weekly

Saturday, December 24, 2005

Merry Christmas, Bitch


I hung up the phone and merged back into traffic. The Gentleman had just called to reschedule our date for Friday. Apparently his company was planning to let several people go (Why not just say ‘fire?’ ‘can?’ ‘sack??’ I hate the term “letting go,” so self-serving in its design to assuage guilt.)

Forgive me, dear readers. Ahem:

Apparently they were planning to sack several employees on Friday, just over a week before Christmas. Very nice, I thought. I have even fewer qualms about taking money from him. Not that he’s a bad person, but that, as a cog in the corporate wheel, he’s lost any professional autonomy he might ever have had. He’s the one who fires people on December 17 when they’re counting on holiday bonuses. I kind of hate him a little bit.

Because of the HR work which must be done, The Gentleman wanted to reschedule our date for the following Wednesday, four days before Christmas. Naturally, I was expecting a nice holiday bonus as well, and expecting it earlier than then. I agreed to the date, saying I hoped nothing else came up, it being so close to the holiday weekend. I also knew there would be a good chance that I’d have my period, but I wasn’t going to say anything on that subject.

I arrived at the hotel, parked the car outside the rear entrance and finished my phone conversation. The Gentleman met me at the door and looked genuinely happy to see me.

I’d been psyching myself up for this; I was in no mood to be sexy. First, my period did arrive the day before, and I was not going to be exposing my pussy to him. If our regular date had fallen during the week of my period I would have told him ahead of time and rescheduled. But he called me with less than 24 hours notice and cancelled our date. So, in my estimation, he is damn lucky to get whatever he gets.

Secondly, my personal life was causing me grief. I'd had a fight with the guy I'm seeing. I was distracted, lonely and mildly depressed by it. I didn’t want to have to be “On.”

But I switched it on. I reasoned that it might be just what I needed—a good, swift kick in the ass to jar me back to myself.

We walked into the room and I started unpacking as he came up behind me and ran his hands across my shoulders and ass, kissing my neck.

“I missed you. It’s been such a long time.”

“I know. How was your day on Friday?”

“It was awful. I hate doing that, especially before the holidays. But I’m not sure which is worse: firing people before or after the holidays. It’s hard either way."

I nodded in agreement as he said, “But I am so GLAD to see you!” He buried his face in my neck and I pulled back.

“It’s really a shame you cancelled our date last Friday, because you know what?”

He looked at me quizzically.

“Today my panties are not coming off.”



Let him think i am punishing him for cancelling on short notice. Maybe my time will be better respected in the future.

I stripped down to the ensemble he’d given me last time. I left my black knee-high boots on. They looked awesome with the stockings, garter belt, g-string and push-up bra. Cara was back: coy, sexy, flirty me.

“Oh, my god, you look so gorgeous.”

“Well, you have very good taste!”

I started pulling out toys, leaving the pièce de résistance: a strap-on dildo harness. I was a little wary of how he might react to that, even though he’s given his ass to my vibrators and butt plugs and fingers.

After I’d selected the playthings, we started kissing. I don’t know if he’ll ever be a good kisser, let alone great. It’s like he is embarrassed and unsure every single time we kiss, despite my best efforts at instruction.

I want to slap him. I want to humiliate him. I don’t.

His fingers slide the cup of my bra down, exposing a nipple. He licks it and then sucks. I can’t even feel it. I am standing between his legs as he sits on the bed. I lean my chest forward to his mouth and slide my knee up to his crotch. I kneel down and suck his semi-hard cock until he is about to come. I push him onto the bed and blindfold him. Not so he won’t be able to see; I don’t care if he watches me, and the scarf is very sheer. He could look at me if he wanted to; I realize now that it’s more so I don’t have to look at him, so I don’t have to answer the questions in his eyes.

I move to kiss his nipples, tracing each one with my tongue and gently biting. I slide a clamp onto each and lube his ass while he plays with himself. I cover an egg vibrator in a condom and push it into his hole. As I turn on the vibe he moans.

“Oh, I like this so much.”

“I’m glad.”

I use another mini vibrator to tease his nipples and the head of his cock. His hands move to my panties. I pull away. I sit next to him and give him my tits. As he softly sucks, I turn up the vibe in his ass. Finally his sucking is harder and faster. Finally I am enjoying myself.

“Cara,” he asks breathlessly, “do you think you might be able to use a vibrator in my ass? I think I might be ready to be fucked.”

Now a grin came to my lips. I couldn’t help it.

“Baby, if you want to get fucked, I can do better than a vibrator. Stay right there.”

I walked to the bag and pulled out the strap-on. Once I had it in position I told him to uncover his eyes. He pushed the scarf up to his forehead.

“Would you like me to fuck you with my cock?”

“Oh, my god…why am I so turned on by that?”

“Don’t ask questions, just tell me. Yes or no?”


“Very well. I want you to roll onto your stomach, bend your knees and spread them as wide as you can. Your chest to the mattress, your ass in the air.”

He did as instructed and I slowly removed the egg from his ass. I wrapped it in a towel and squirted lube into his crack.

“Lube yourself. Inside and out.”

I put on a glove and lubed the fingers.

“Don’t be nervous, it’s just my fingers. We’ve done this before. Deep breaths and push down a little bit…there. How are you?”

“Good,” his voice was quiet.

I put another finger beside the first, checking the angle of penetration, the slight jog to the right that his rectum takes after the first couple centimeters. I moved the fingers in, out and around, massaging and relaxing the muscle ring to accept the size of my dildo.

With my two fingers in, after several minutes I placed the head of my condom-covered cock at the entrance. Slowly pulling my fingers out, I replaced them with the dildo, easing in, curving right. He tensed, and his breathing changed. I stopped, holding position.

“Take a deep breath and tell me how you feel.”

“Uh, okay…”

“It shouldn’t hurt,” I squirted more lube on the three inches or so of my cock which were outside his ass, and spread it around his hole.

“No, it doesn’t hurt. It’s just…different.”

“Okay, that’s good. I’m going to go very slowly and you tell me if you want me to stop.”

I pressed slowly in, his ass swallowing my cock. I held it there, gently pulsing. He sighed and smiled. I held his hips and started fucking in short thrusts, very slowly, very gently, gradually increasing speed.

“I can’t believe I’m doing this,” he said.

“Believe it…enjoy it,” (‘bitch,’ I thought.)

My thrusts became deeper and faster. I was pumping his ass full of my cock and he was enjoying it.

After about five minutes he’d had enough. I pulled out and went to the washroom. I cleaned the toys, wrapped the condoms and glove in toilet paper and tossed them into the trash, rolled the soiled towel up and put it on the floor under the sink.

When I returned, he was lying on his back, smoking, still wearing the nipple clamps and the scarf pushed up to his forehead. He looked ridiculous.

“Hey, babe. I thought I lost you in there!”

“No, but good sex etiquette demands clean toys and a tidy hotel room,” I said, as I removed the nipple clamps. He sucked his breath as the circulation returned to his nipples.

“I really wanted to cum, but I lost my erection while you were fucking me…I still can’t believe I took it up the ass!”

“Hah! You took it like a MAN!”

I looked at the clock and saw a little time remaining. I took his soft cock in my mouth and sucked him off. He came in my hand.

As I dressed he wondered if we could meet during the week between Christmas and New Years. I told him it would be a pleasure. But I wasn’t betting on it.

Back home I continued the conversation I was having when I arrived at the hotel.

-Well, how was it?
-Bearable. I fucked him with my strap-on and called him my bitch.
-Wow, congratulations on crossing that threshold!
-I know, but somehow I don’t feel any better.
-Odd; fucking ass for cash always seems to make me feel better.
-I’m just in a funk. Everything that’s going on with the boy, you know?
-Yeah, sweetie, I know. Anything I can do?
-Nope, you’re awesome. I love you.
-I love you, too. You’re totally awesome. And boys are stupid.

It’s good to have friends.

Happy Holidays, Bitches.


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