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Shy woman comes across in style

It was the Christmas party, in the offices, and I had been getting stuck into the wine. Caroline had been nursing the same glass for half an hour, so it was no longer beaded with condensation, but dry outside and warm inside.

 “Does sex have to be part of a wider arrangement? Can’t it be the arrangement itself?”

I thought it was a reasonable question, and one that any reasonably intelligent woman could accept without getting upset.

“And how do you come to that arrangement?” Caroline countered. She was the chief executive’s personal assistant at the firm I worked for in Trinidad. She was a Trini, but of British heritage, a century or so removed from the old country. She had a nice tinge of the local version of English, which was not just pronounced differently but used different grammar and even vocabulary, making it hard to understand some people.

From Caroline’s mouth it was just a bit of local colouring and perfectly intelligible. It was pretty much how she looked, in fact. Her European features had survived an upbringing in the tropics and she wasn’t even sun-burnished. Compared to her, I was dark, because like many newcomers I spent as much time in the sun as I could, while the locals stayed out of it, both for health reasons and because there was no novelty factor. They had been able to go to the beach any time of the year their whole life, and in fact many of the Trinis I knew just didn’t bother with it at all.

 “Well, you discuss it,” I said. “Or you meet someone through a dating site.”

“You go on dating sites looking for sex?” she exclaimed.

“Everyone is looking for sex,” I protested mildly, for her benefit. “It’s on the list somewhere. And there are sites where it’s more open.”

“What do you mean?”

“I mean there are sites where that’s the whole point. That’s why people go there.”

Caroline raised an eyebrow.

“Women as well as men,” I said with a smile which I kept brief so it didn’t look like a smirk. “Most people are only bothered about how it looks to people who know them. They wouldn’t admit it publicly, but as long as no one knows, that’s okay.”

“And you have been on one of these sites?” she asked rather nervously.

“Yeah.”

“Meet anyone nice?”

“Yes, actually,” I said. “You’re as likely to meet a nice person on there as you are anywhere. It’s just that you get down to brass tacks a lot quicker.”

And that was where the conversation ended, as Caroline was swept away by a colleague from the accounts department.

I hadn’t thought about it much since that time, just the occasional flicker when I spoke to her when trying to get through to the boss on the phone.

She was friendly and efficient. Reserved: not exactly shy but quiet. A churchgoer – and that’s another preconception people have: that religious people don’t have sex. Of course they do. As a matter of fact I had met a couple of women through a Christian dating site in the UK and ended up in bed with both of them (separate women, separate occasions, although they were quite similar, being black, forty-something and divorced.)

So even if Caroline thought she wouldn’t be on my radar, she was. Is that wrong? It’s the kind of question I would have liked to ask her. I sensed that she had enjoyed our sex conversation, got a little kick out of it that she wouldn’t display, for appearances’ sake.

Now here we were again: same offices, same crowd, for someone’s leaving party. I had come over on the early boat, from Tobago, the little sister island where I was based. I liked the odd overnight trip to Trinidad and usually managed to find a decent hotel room going cheap on one of the last-minute sites. On this occasion it was the Hilton, no less, for about fifty dollars.

Caroline was slim and demure in a sensible trouser suit of navy blue cotton. She was quite classy, I thought. I gathered she had never been married and it puzzled me a bit. She was prime wife material.

I was hanging around by the buffet when she appeared at my shoulder.

They’re nice,” she said, pointing to the vol au vents.

“Yeah. Trouble with these do’s is there’s some food but not enough,” I said, passing her a little curiosity loaded with tiny black shiny balls, which tasted salty and was apparently caviar. Caroline took it with her teeth, straight from my fingers.”

“Mmph. You’re right. You’re still hungry when you leave.”

“I’m going to have dinner later,” I said. “How about you?”

“Could do with something,” she agreed. “Where?”

“Back at the hotel,” I said. “I’m going to order a taxi right now.”

Caroline put her hand on my arm and said “I can give you a ride.”

Now, maybe I’m naïve or over-cautious or something, but I try not to read too much into such things, so as we drove through the relatively quiet evening street towards the Savannah, I was making polite conversation, that’s all. Sure, I glanced at her legs and enjoyed the way the seatbelt parted her breasts, but I didn’t touch her.

When we reached the hotel she drove into the car park rather than dropping me at the entrance.

“You coming in?” I asked.

“I thought we were having dinner,” she said a bit nervously.

“Great!” I said. “Yeah. We should have time to get downstairs and do the buffet thing.”

That was the cheaper option, but still quite fancy. We skipped down the stairs and got organized.

“So, had any interesting dates lately?” Caroline asked lightly. I had in fact met a girl in that very hotel a few weeks earlier and had a very nice time, but I didn’t want Caroline to think I was a wham-bam sort of guy.

“There was someone a while back,” I said.

“Nice?”

“Yeah.”

“And what happened to her? Do they turn into relationships or is the arrangement purely for the here and now?”

“I suppose you have lower expectations,” I admitted. “If you meet through one of those sites. But everybody’s looking for love too. It’s just harder to find.”

Caroline nodded sagely.

“You meeting her on this trip? I’m not interrupting, am I? Is she going to appear in a minute and give me a slap and kick my white ass out of here?”

“No,” I said, and gave no explanation. “No, tonight you have my full attention.”

“Oh good,” she said, amused. “So maybe you can show me how to fill one of these things in.”

From her cavernous bag she produced a Samsung tablet and asked me to do the wifi code. Then she called up the very site I used and logged in. I was a bit concerned that she might find my profile, or that she had found it already and was intent on embarrassing me.

But she didn’t. She called up her own partially completed page. She was called Headintheclouds.

“What do you put on these things?” she asked.

“Depends what you’re looking for,” I said.

“Let’s say I’m looking for a one-night stand with the possibility of a future,” she said.

I moved my chair around the table so we were sitting together. She had filled in the physical description and the interests (volleyball, swimming, carpentry).

“Carpentry?” I queried.

“I’m an only child,” she said. “My Dad used to teach me things and I enjoyed it.”

“General intro,” I said. “ How about something like ‘I’m a woman, still young, attractive, fit and healthy. Looking for some fun – put an exclamation mark in brackets there – with a 30-something guy. Intelligence more important than looks – that okay?”

“Perfect,” she said. “Although does that mean I get all the ugly ones?”

“It means you get the ones who think they’re intelligent or who haven’t read it anyway, just looked at the picture."

“Well let’s see if there are any suitable guys on here already,” she said, ticking boxes on the search menu.

When the results came up, sure enough I was on it. Not my real name, of course, and no face pic. Caroline looked at a couple of studs, who both turned out to be all body and no mind, as she put it. Then she came to Bagonow. That was me. I lived in Tobago now. The username doesn’t matter once someone has looked at the profile. It’s more important not to put people off than to try to pull through the power of one or two words.

“White guy in Tobago,” she mused. “Sounds interesting. He likes… oh my god, licking women’s middle bits, front and back.”

“Well at least he’s upfront about it,” I said. “Nothing wrong with that, anyway. I told you, you just get to the nitty gritty quicker. He doesn’t sound totally stupid, does he? Can string a sentence together. Why don’t you send him a feeler? Just say hello and he sounds interesting. That’s what you said.”

“What if he turns out to be a psycho?” she said nervously.

“He’s got no access to you,” I explained. “All he has is this site. No name, phone number, email, nothing.”

A waitress appeared and started clearing the table, so we decided to leave it till later.

“We could go upstairs,” I suggested.

“What’s upstairs?”

“My room,” I said simply. “We won’t be disturbed there, so we can get you up and running. You’ll need a picture. Got one?”

“You can take one,” she said bravely as we headed for the stairs.

As she stood up one of the heels on her shoes broke.

“Damn,” she said, fiddling with it.

“Take them off and walk barefoot,” I said. “It’s a hotel, it’s clean and you’re a guest.”

My room was a long walk and I could see her enjoying being the carefree girl with her shoes in her hand. She seemed to loosen up because of it, and by the time we got inside she was quite breezy.

I took a bottle of white rum from the table and poured two Cuba Libres – rum and Coke by another name.

“What kind of picture?” I asked.

“Me in my bare feet,” she replied. “Let me take the jacket off.”

She sat on the edge of the bed with her legs crossed.

“No face,” she warned. I took a couple of shots and showed her.

“God, I look frumpy,” she said.

“Undo a couple of buttons on your blouse,” I suggested. She looked at me warily but complied. A warm, inviting patch of flesh appeared, along with the edge of a black bra.

“Much better,” I said, showing her the result. “Slightly cheeky but classy.”

We uploaded the pic to her profile and quit the site.

“Now we just wait and see,” I said. “By the morning you’ll have loads of interest, I bet you.”

“Well thank you for being my mentor,” she said, putting her hand on my knee as we sat together on a little settee. “Maybe I’ll find someone as kind as you.” The air turned heavy and we both fell silent. Then I put my arm around her and she snuggled against me. I kissed her and she kissed back.

This was the same very conservative woman I had known vaguely for a couple of years, so I wasn’t counting my chickens just yet, but I caressed her neck and then kissed it and she squeezed my knee.

Encouraged, I slipped a hand into her blouse and felt her breasts through her bra. She adjusted her position so I could unbutton the thing and she slipped out of it elegantly.

Caroline was now naked from the waist up. She had nice firm breasts, fairly small – the kind she would probably have ordered if you could choose your body parts. Feminine, womanly, but not at all tarty. Something for a man to enjoy when he got there, but not the reason he came to her in the first place.

I moved my head down and sucked her nipples, first the left and then the right. She made little sighing noises to show she was enjoying it, and her hand moved up towards my crotch, but she was waiting for me to move into that area before she did.

I put a hand directly on her warm, mystical mound, rubbing the slit gently, and she responded by taking a trousered handful of male parts in her hand.

We were kissing happily and the flickering of tongues was generating power in my cock. She traced the outline of my erection between her thumb and forefinger as I fumbled with the catch on her trousers. You never know quite what you’re dealing with and I didn’t want to seem clumsy, but it turned out to be a large button that gave way easily, and I slid the zip down far enough to get my hand in her pants. They were small and delicate, lacy. Her pubic hair was trimmed but still much in evidence as I ran a finger through it and into her slit. It occurred to me that there was no excuse for not finding the clitoris when you went right over it on the route to the hole. Maybe the old-timers who are accused of not pleasing women in that way were just plain ignorant – didn’t know such a thing existed.

I played with the little knobby thing for a minute or so and Caroline became super aroused.

The time for talk was past. I would have liked to ask her how she could be so comfortable with this when she seemed so unsexual in her day-to-day life. But we’re all full of contradictions, I suppose.

“Stand up,” I said firmly and she did, wriggling a little to allow me to slide her trousers and pants down to the floor. Shoeless, she stepped out of them neatly.

It was a thong. I was surprised and a little shocked that Miss Prim should be wearing the underwear of the seductive. I pulled the sinful thing down and off.

I sat her down on the edge of the bed and undressed right in front of her. She watched bashfully as I slid my underpants down and my erect cock sprang to life before her eyes. I pulled her towards me so her face was in my crotch, and I stroked the back of her head.

“There’s just one thing,” she said in a very controlled voice, distancing herself from the situation. “You can’t get inside me tonight.”

“Are you on?”

“No,” she replied. “Just not yet, okay?”

I knelt in front of her and kissed her tenderly on the lips. “Okay,” I promised. Then I pushed her back on the bed and set about achieving at least something, if the ultimate prize was not on offer. If it wasn’t here period, then at least she should be open for a licking.

As my head went up between her legs she leaned back on her elbows to watch. My nose touched her neatly coiffed pubic hair and I smelled the unmistakable, irreplaceable aroma of vagina. Her womanly juices were glistening within her labia and I licked and sucked them.

She lay back, quivering with sexual excitement as my tongue and lips played with her, teased her and demanded her essence, which her body dispensed freely into my mouth. My tongue went way up inside her and she arched her back, as if to give me room. Then she gave a little “oh” and shivered as an orgasm raced through her.

She held my ears and stroked them as I continued to lick and suck her, and then she raised her legs, higher and higher, gripping them with her hands, and moved her hips until her pussy was facing the ceiling and her arsehole was staring at me. This was not the movement of a shy woman; she had crossed a line in her mind and was going to get what she wanted from me.

I plunged my face into her crack and she gasped as I licked her arse with lewd abandon.

“Oh yeah, oh yes, oh shit,” she squealed as my tongue in her secret hole drove her crazy. “Fuck, yes, oh, lick my bum, I love it, I love you.”

Utterly out of control, Caroline rubbed her bottom into my face as she climaxed with cataclysmic intensity.

And then she was finished, and she lay back and extended her arms to collect me.

“It’s you on that site, isn’t it?” she said breathlessly. “The one who likes to kick women front and back.”

“Might be,” I said. “You like it?”

“I just had the most incredible orgasm,” she said, “in case you didn’t notice. You’re the rudest, dirtiest man I’ve ever met.”

"I'll take that as a compliment," I said, runing my finger through her dark valley and kissing her at the same time.

 

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