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.

Saturday, December 17, 2005

Whore Persona

Nearly six weeks since our last meeting, The Gentleman called with some mildly disturbing news.

He’d gone to the doctor after weeks of stomach distress, and called me with the conclusion that he had to make some changes in his life. Seems he was stressed and his tummy wasn’t cooperating. The call came as I was making my rounds at Whole Foods one afternoon.

“Hey, baby. What did the doctor say?”

“He said that I needed to reduce the stress in my life”

“What does that mean?”

“There are a lot of things that are weighing on me financially…my business and other burdens are putting me under a lot of stress. And I've been thinking about you a lot. I really miss you.”

“Well, we should try and fix that!”

“I just don’t know how feasible it is for me to keep seeing you when I have to put some of my own finances into this business…I guess it’s not realistic to expect to see you without some payment taking place…”

“Oh, baby…that’s what this is about?”

“I just don’t know how I can afford a weekly date with you and still meet my obligations to my company.”

“Listen, you need to take care of your health. That’s the most important thing. And if it’s too much for you financially right now, that’s fine. You just call me when things have calmed down, okay?”

He hesitantly agreed, and I ended our conversation, saying he didn’t need to worry, that I was fine, and that I hoped to hear from him soon. I think he would have stayed on the line indefinitely if I hadn’t hung up.

I got to thinking: Maybe our weekly arrangement was a bit much. What if we only met once or twice a month? Obviously, something would be better than nothing, and our dates had afforded me some luxuries I hadn’t had before. He definitely needed the outlet, and I was having so much fun…

He was not going to make the first move; I knew from our sessions that he was not exactly forthcoming in his opinions. I decided to email him.

Hi, G.

I've been thinking about our phone conversation yesterday and I've been a little troubled by it. Obviously, you have to do what's best for you. If it's not feasible for you to continue getting together I understand. But I don't want you to feel like our original agreement is set in stone.

I do enjoy being with you. I want to be as flexible as I can be for you. Perhaps you'd like to consider whether a different arrangement (less often, or for less time, or both) makes any sense.

This has been fun for me; planning our dates, introducing you to new experiences, learning what excites you. I wonder if it could possibly continue, with an adjustment of terms. There are lots of changes which could be made to make it a bit easier on you financially, and (if your doctor is to be believed) alleviate some of that stress while releasing tension!

I guess what I'm saying is, think about it. And be honest. Write me back and tell me what you think. If 60 or 90 minutes sounds better than two hours, if twice a month sounds better than once a week, whatever.

As I said on the phone, I am disappointed by this, but I understand. I just know how frustrating it can be to come so close to something, only to have it pulled out from under you. I felt like we were moving things up a level sexually, and it's sad to have that end so abruptly.

Whatever you decide let me know.

Have a good weekend,

So he responded. And we set a lunch date to discuss new terms. Of course, he called two days before our date.

We agreed on a restaurant, the one we'd met at before. We discussed financial arrangements and thought that twice a month for 90 minutes might be something to try.

I was happy he’d come around. I thought it was silly to stop things just when they were getting good, and I had the feeling he really wanted to continue but was unsure how to approach me about it.

He was very excited and happy that I had come back with alternate suggestions. He probably would not have done it, even though he had thought about it.

“Well, I am nothing if not straightforward,” I said.

He asked if there were supplies he should bring. I reminded him that last time he broke my favorite vibrator. He wrote down the model and then asked for my bra size.

“34 D or DD, depending…what are you planning to do??”

“I thought that maybe you’d like to wear some lingerie for me if I brought it.”

“Oh! I’d like that very much!”

The next day we met for lunch. I ordered a vodka tonic and didn’t pay attention to the price of my lunch. I figured that if I was going to be getting paid less in cash, I should order whatever I wanted.

In the room, I took off my shoes and coat and laid my handbag on the floor. I put my toybag on the dresser. There was a huge gift bag on the bed which I pretended not to see. We kissed and he took my hand and led me over to the bed.

“Oh, my goodness…what is this?”

“This is your early holiday present, Cara. I hope you like it.”

In the bag were two boxes. I picked up the large one first, naturally. It was a restraint system which consisted of four nylon and Velcro cuffs that could be attached to any point on a spiderweb of nylon straps that are secured to the corners of a mattress. It looked complicated, but when we straightened it out and laid it on top of the bed it looked like it could be fun. The restrained person could be repositioned easily onto their knees or back or tummy simply by refastening the cuff release.

“Okay, I am liking this…does this mean you want to restrain me?”

“If you’d be willing, I’d like to very much. But you still have another gift! You have to open it!”

The smaller box was pink with silver writing. I slid the lid off and peeled back the tissue paper. I gasped. It was so pretty—an entire ensemble of lingerie—bra, panties and garter belt. All black.

“Oh, my god, it’s gorgeous! I love it! Thank you!”

I gave him a kiss and held up the bra to my chest. I looked at the tag. It was the perfect size. This was going to look fabulous.

“But, baby, I didn’t wear stockings; how can I model this for you…I guess with just the bra and panties?”

He grinned and reached into the box, moving the paper to one side. A package of black stockings lay underneath.

"Well, don't you just think of everything?!"

“Oh, you forgot something else, Cara.”

He held the big bag angled toward me and I reached in and felt it: my new vibrator. Yippee!

“Why don’t you go get changed?”

“I’ll do that, while you load this baby up with batteries…’kay, hon?”

I gathered everything into the box and carried it to the bathroom. It took a while; it’s been years since I’ve worn a garter belt and those hold-ups are tricky, especially the back ones.

I walked out and stood in front of him.

“Oh, my god, that’s gorgeous.”

“It is! You did very well! Hey, watch me—I’m walking now…”

I pranced slowly to the other side of the room and turned.

He gulped and came over to put his arms around me. We were standing in front of the small dresser with the mirror. He told me to look at myself. Then he said, “I guess I should probably get undressed, now, huh?”

“You do what you want, baby. All I know is that these stockings are staying on.”

I sat on the bed and watched him undress to his shorts and socks. It is so endearing to me now that he leaves his socks on. I figure if he’s that uptight about his feet, I don’t want to see what’s underneath the Gold Toes.

We sat on the bed and he stroked my legs through the stockings.

He told me I smelled good. He kissed me. My feet were in his lap and he pushed my knees apart and leaned me back toward the pillows. He turned on the vibrator and lightly touched my clit through the panties. I gasped and moved around to get it to the right spot.

I know this vibrator, and I can get off in record time with it.

“Oh, babe, your panties are soaked…”

I guided him with the vibrator, pinching my nipples and sitting up to kiss him once I’d come. I was smiling, thinking how happy I was going to make myself later when I got home with my new replacement.

He unhooked my bra and tossed it to the chair. He helped me off with my panties and held them up to his face.

“It’s nice, huh?”

He nodded and went to the restraints. He asked me to lie down and then struggled to detach the cuffs. I helped him out, telling him where to put the release straps and even wrapping my wrists and one ankle myself.

I told him where to find the buttplug in my bag and asked him to turn up the music. He brought the bag to the bed and rummaged through it.

"Cold Hard B****" by Jet was in rotation on my iPod.

I was spread out on the king-sized bed wearing the garter belt and stockings. He stroked my body down to my pussy, raising my knees and spreading them.

“You have such a pretty pussy, Cara.”


“So pretty and pink and wet…”

“Uh-huh…” (Please stop talking about it and do something, would you….)

He dove in, licking around my clit, up and down my slit to my ass. (Now we’re talking…)

The Gentleman takes his time eating pussy. I’ve learned that it is really the reason I’m here. He isn’t as interested in his own orgasms, but loves to give them to me, so I accept it like another gift. He is a willing pupil, thank goodness, because I was directing him the entire time (to the left, up, now put your fingers on my g-spot and move them like this…).

I got off again and he exclaimed about how wet my pussy was again. Then he told me how nice my breasts were and asked if I’d ever tried “those nipple clips.”

I laughed, “Yes, there are some in my bag. Would you like to put them on?”

He jumped and grabbed them. I instructed him on how to pull my nipples up and attach the clamps with the slides. The pain was sharp at first, but yielded to pure sensation. I sighed.

I swear to God, I heard his cock stiffen.

“Can I put the plug in your ass?”

“Yes, just put a condom on it and use plenty of lube.” (God, I wish I didn’t have to talk so much…)

The upside was that he did everything I told him to do. He learned about the ultra-sensitive spot just to the right of my clit that sends me, head thrown back, over the edge with barely a “hello.”

He wanted to fuck me.

(Five dates and I was getting fucked for the first time. Not bad.)

He put on a condom and released my ankles. He fucked me. Pure friction. Two minutes and he was done, shooting into the condom

I don’t mean to sound put off by it; the fucking was fine, it just didn’t get me off. I didn’t really expect it to, but he was blissfully happy, and that’s what we were going for, right?

We’d gone way over on time, but I chalked it up to a nice reunion after so many weeks without a meeting. Plus, those garters proved pretty tricky. All told, I figured he’d spent a good $200 on gifts; add another $50 or so for lunch, and I wasn’t troubled by the extra time.

I gathered up my booty and dressed quickly. He apologized profusely for not paying attention to the clock, since he was the one “in control.”

I laughed to myself that, in between orgasms, there I was, all tied up with a plug in my butt, clamps on my nipples and a dick in my cunt and I was still bossing him around. I guess it’s just my whore persona.

It’s interesting to me that I behave so differently in this situation than in every other sexual relationship I’ve ever had. I am very easygoing, rarely taking charge during sex. I love being forced to suck my boyfriend’s cock while I’m tied up, for example. With The Gentleman, though, I don’t even think along those lines. I am the writer, producer and star in this show. I really, really like it.

I’m already working on the script for this week.