Sugar Baby Weekly

Thursday, October 20, 2005


Today, for our fourth date, The Gentleman was expecting some exta fun. I’d finally let him touch my pussy last week, and when I left him, he was singing the praises of the Almighty G Spot.

I enjoy the familiarity of our encounters: I leave my house, on the way to the hotel, he phones and gives me the room number. I knock, he invites me in, we chat, peppering our conversation with hand squeezes and kisses.

This week I am wearing jeans, a wrap-front top and boots. The sky was turning grey and clouds were rolling in.

I had plans for him this time. As it happens, I can’t have sex today. Luckily, The Gentleman is interested in experiencing more than that. He likes that I have more experience with kink, and am a patient teacher. In that spirit, I have decided to give him assignments to complete for our future meetings. These may be nothing more than to walk into a sex shop and buy a bottle of lube, or they might be more involved; kinkier.

As I am exploring my dominant side I am becoming more comfortable telling him what I would like him to to for me. I think I am becoming quite good at it. As I unpacked my iPod and speakers, I said, “You know, on the drive over, I really noticed how sore my neck and shoulders are. You have no idea how much my feet and legs ache...I would like you to massage them for me.”

His eyes widened, and he smiled broadly, “Oh, yes; I would absolutely love it. Can we start now?”

“Of course.” I moved over and sat on the ottoman in front of his chair. He began rubbing my shoulders and my neck. I leaned back (or, rather, he pulled me back) onto his chest. His hands moved around to cup my breasts through my top. “Does this hurt?

“No, but I need a drink, and the television really shouldn’t be on, now, should it?”

He got up to retrieve my drink and turn off the set. I stood, dropped trou and waited for him to turn around, “I’m ready for my legs now.” I leaned back on the bed and he undressed to his uniform: white t-shirt, blue boxers and black socks.

“Cara, those panties...”
“Aren’t they pretty? I’m glad you like them, because you’ll get to look at them for the next two’s the massage oil. Start with my feet, please.”

He did, and when the fronts of my legs were done, I flipped onto my tummy. I was still dressed in my camisole and g-string panties. The Gentleman massaged my legs and ass, really getting into the last part.

During the massage my thoughts roamed to things I’ve got to do in preparation for the coming week, how to best deal with my mother’s increasing need for attention in the face of her own mortality, whether the new hair foam I bought is really as good as the company says. And how this is all very pleasant, but will I have time to get to my next meeting? I wonder how the novel I’m reading turns out. How long will it take to finish knitting that scarf I started two months ago?

I catch myself and let my feet roam over to rub his erection through his shorts. The wetness there, the smell of his sex and mine took over my senses. I reached down to my panties and slipped my fingers inside. My breathing was shallow, and as he kneaded my backside, I tickled my front, arching my back and raising my head to kiss him.

“Cara,” he said, breathless, “can we talk about anal?”
“Have you ever fucked a woman’s ass?”
“No, never.”
“Have you ever been fucked in the ass?”
“No, but I’m intrigued by the idea.Why?”

I’d packed a vibrator.

“Well, I am a firm believer that in order to effectively fuck an ass, one should be well acquainted with the sensation of being fucked firsthand. I would be very happy to introduce you. Would you like that?”

“Oh, yes. I think I’d like that very much.”

I walked over to my bag and sat down beside it on the floor. first, I held up a plug. “Now, this is just a bit big for your first time, I think,” he nodded quickly, “that is a little frightening, yes.”

“But this,” I held up a wand vibrator with a bulb on the end for g-spot stimulation, “this would be perfect.”

I sheathed the vibe in a condom and climbed up beside him on the bed with the vial of lube.

He was stroking his cock and had taken off his shorts. I started speaking softly, slowly, explaining that I would start with a small finger, very gently opening him up to larger things. He pulled his legs up and I lubed his arse and my fingers. As I massaged around his hole, I talked about breathing, relaxing. My third finger went in without resistance. I moved around and in, slowly, listening for changes in his breathing.

“Oh, my god, that feels so good...”
“I’m glad, baby. Are you ready for something bigger?”
“Oh, yes...please.”

I took the vibrator in my right hand, placing it against the base of my finger already inside. Slowly, I pulled the finger backwards and pushed the bulb of the toy against him. Immediately, his body took it in. I rotated the wand so that the bulb was angled toward his prostrate, “Is that the right spot, baby?” His head was turned, eyes closed in bliss. He nodded, “yes. Oh, my pet, yes.”

I turned the vibe to LOW. Then I moved his hands away from his cock and started sucking it hard. He was writhing under my head, my lips wrapped around his cock, sucking madly.

My Gentleman moaned, louder than I’d ever heard him, “I’m coming....Cara, I’m coming.”

One last suck up, and I turned up the vibe and started jerking him with my free hand. His come shot, spilling onto his stomach and my hand.

His eyes were wide and amazed, his breathing irregular gulps.

“Baby, are you okay? That was so nice, watching you come.”

“Uhh, I don’t know what to say...that was incredible! I’ve never had an orgasm like that!”

“Isn't it incredible? Let me get you a towel; stay right there.”

He towelled off, and, knowing I had a schedule to keep, prodded me to put myself back together so I would not be late.

We kissed at the door. He was still grinning and shaking his head.

“Next week?”
“Next week.”

While I would not have chosen The Gentleman for myself, given our arrangement, he really is the ideal client for a girl like me. He is open to new experiences, likes that I have had adventurous romps and am not opposed to more, and he is genuinely nice.

This consideration (am I hurting you? Can I do this?) is almost annoying sometimes, because he is so concerned with my comfort and talks--sometimes incessantly--about how great he thinks I am, when I just want to go the other route and have mad, silent, crazy playtime.

Still, he is teachable, he enjoys being submissive, and is respectful of the boundaries I placed on our relationship.

Right, I gave him an assignment: He is to wank at least three times this week, one of those in the shower with a finger in his bum.


  • At 8:47 PM, Blogger Stanley said…

    He's a lucky man, your Gentleman. And you're clearly a great teacher. It is fun to read about your sessions.


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