One night with Helen by Twister98

I had no doubt she was using a fake name on the website’s profile, after all, how many people do use their real names on adult sites? But Helen Troy seemed a bit on the nose, she didn’t really look Greek in any way to me when we met. Helen was not wearing much makeup, some subtle shade of red lipstick seemed to be about it, her hair was tied back but showed plenty of curls while she wore what might very well have been office attire. A crisp white shirt crossed with pin stripes, the top three buttons undone leaving a hint of cleavage that would only really catch your eyes if you were standing next to her.

Her choice of skirt however must have quite the head turner if she actually wore that to the office. Short, a good inch above her knees showing off the shiny gleam of her stockings. Like her jacket it was grey, and form fitting, stretching to allow her to take long strides in her three inch heels as she entered the cafe.

The effect left me wondering what field of work she was in and how I could get a job in her office. I quickly checked myself to make sure my tongue hadn’t unrolled onto the floor and made sure my legs were crossed, then I raised my hand to get her attention. I felt very much out of her league dressed as I was in just blue jeans and a white T shirt, my jacket over the seat I’d taken.

Helen smiled as she saw me and slinked her way over to me. I remembered my manners and stood up offering my hand for a shake, which she accepted as we introduced ourselves, then pulled me towards her for a quick peck on our lips. I could feel something left behind on mine as we pulled away, I could almost taste it but my nose picked up the faint scent of mint. Some sort of lip gloss maybe? Either way my heart seemed to perk up a bit more.

“Please, take a seat,” I said as I waved a hand at the chair opposite mine. To my surprise, and delight, she took the chair to my immediate right, crossing one leg over the other. I could hear the sounds of her stockings gently rubbing against one another. “Can I get you something? Coffee? Tea?”

We had a long chat as we ate our sandwiches, never once about anything dull. Somehow I think she could have made talking about the weather… interesting. Helen had an interesting manner of making sure she only ever took a small amount of the sandwich between her lips, almost nibbling the corner before slowly closing her mouth around it.

“Have you had much luck on the site?” she asked. I shook my head.

“Not really, I’ve not been on long, maybe two weeks.”

“No one else has sent you any messages?”

“Oh there were messages, usually the same request to go to another site to prove who you are. You know, by providing your bank details.”

“Oh god,” she laughed daintily. “Are they still trying that one?”

“Then there were two women who seemed genuine, but they never showed up for the dates.”

“Cold feet, it happens.” She gave me a curious look, like she was reading my mind. “Any others?”

“Not on this site, there was another where I got chatting to this one woman who claimed…””Yes?””She claimed to be a shrink of all things.”

“Doing some kind of study of online dating?”

“If she was, she never said so.” I paused as I recalled some of the details. “But she did introduce me to some online friends of hers on that site.”

“That sounds interesting,” she gave me an inquisitive look. “Where did that go?”

“Well, I got suspicious. All the people seemed to be writing their messages in the same style.”

“Ohhh, I see, she was using puppet accounts then?”

“Yeah, that’s about as good a name for them as any. But they all seemed to close down, and then you’d get a new profile days later, with very similar pics and the same sort of stats and interests and what not.”

“Well, sounds like she was a bit of a cock tease,” Helen said matter of factly. “You wanna go for a walk? The park over the road is rather nice.”

“Don’t you need to get back to the office? Your lunch break must be nearly over.”

“I took a half day, I had a good feeling when we got in touch,” she said as she uncrossed her legs before she stood up, patting down her skirt to remove imaginary crumbs. I could hear the sound of her stockings rubbing gently against each other and wondered what it would be like to have those legs wrapped around my ears.

We’d already paid for our meal so we left and enjoyed a pleasant walk in the sun filled park, a gentle breeze took the bite out of the heat. If Helens profile was to be believed, she was 35, 5 years my senior, but barely looked 30. She had a confession to make that I found almost impossible.

“I’m more or less a virgin,” she admitted with a coy smile which made her eyes light up.

“What?” I was flabbergasted. “How?”

“What I mean is, I’ve only had sex once.” I picked up on something in her demeanour.

“You mean with one guy?” She nodded, still looking coy.

“See, I spent years convinced I was a lesbian, so I did lesbian things. Or rather what my girlfriends told me were lesbian things.” We turned a corner in the park, I could see we had the place more or less to ourselves, there were trees and bushes that towered over most of the pathways as well as hemming in the entire park itself. But I could just about see a row of terrace housing at the far end which Helen seemed to be almost guiding me towards. “Lots of kissing, rubbing, feeling, fingering, licking, that kind of stuff.”

“When did that first start?”

“When I was 18, I’ve spent most of my life loving only women, thinking that was all I needed.”

“So, something obviously changed?” she nodded. “Did you come home one day to find a used dildo left out where anyone could see it?”

“Not quite like that, no,” she laughed a little, then took my hand in hers and patted it. “I was involved with two other girls, who I thought were the most beautiful women ever, three ways each night. Then I went off on a work do for a week, came home a day earlier than I expected, and found them in bed with two men.”

“You don’t sound upset?”

“Oh, not now I’m not, but back then, dear god, I just screamed. One of them had a cock in her arse! We’d never done anything back there! I just screamed and ran out the room and sobbed in my bedroom. What was worse, they just kept going at it.”

“Christ! They didn’t check on you?”

“No, not until the next day. Then it all came out, they’d been seeing more than just me, there’d been other girls, more men, groups… I’d always thought before that day that the bed needed replacing.”

“God… when did all that happen?”

“About a year back, I’m over it now, but it did get me thinking. What am I missing?”

“So…” I put two and two together. “You’re technically a virgin because you’ve never had cock?”

“Well, I was, until about a month ago,” she switched from holding hands with me to wrapping our arms together and pulling me closer, those naughty eyes of hers only lit up even more as her smile took on an almost wicked bent. “That was something I needed to try, to find out if I actually liked cock, and it turned out I do.”

“What did you do with the lucky guy?”

“Well, I sucked him, didn’t really know what I was doing there, but he didn’t complain.” She paused again, then smirked. “Then there was The Main Event. It was alright, but he was more the kind to just push it in, then hump away.”

“Didn’t try any other positions?” I realised we seemed to be heading towards the houses at the back of the park.

“No, just held my legs down on the bed, while he mauled my nipples and humped his end away. The sex wasn’t good, but I did like the penetration.” I got the feeling she was holding something back.

“Was that all that happened?”

“Well, he did lick me out, but he wasn’t very good at it.” She took a deep breath. “And the condom came off too.”

“What? Did he slip it off?”

“No, never had a chance. His hands were always busy, holding my legs open, holding me down, playing with my boobs. Speaking of which, is titty fucking normal?”

“If you have the boobs for it, and you both like it. Did he?”

“That’s how I know the rubber came off.”

“He probably pulled out of your pussy with that aim.”

“Maybe. Either way, I’m not seeing him again. I want a younger model,” she smirked, then pointed at a house in the middle of the row. “That’s mine, you want to come in for another coffee? Or something stronger?”

“I was thinking of something wilder.”

“What a coincidence, so was I!”

We made our way up stairs to her bedroom, having barely paused to close her front door or take our shoes off. She was clearly an expert in undressing her lovers as he had my shirt off over my head with a strong tug at the back of my collar before she was pressing her still clothed body against my naked chest. Our hands roamed over each other’s bodies as our lips played with one another. My hands claimed a spot on each of her incredibly tight butt cheeks, I’d barely had time to spot her bicycle downstairs, but as my fingers made their way over her back towards her neck I could trace the contours of her muscles on her very slender frame.

Her hands were already tugging my belt free from my jeans as our tongues started playing tonsil tennis, she pulled me towards her bed by the top of my trousers while my hands pulled her skirt up over her hips and waist, while she somehow pulled off her jacket top in one move, flinging off to one side while I stared at the sight of what lay between her rolled up skirt and the tops of her shiny black thigh high stockings.

The barest, most silky smooth looking pussy I had ever seen. Clearly a waxing job given the lack of any bumps or nicks, or maybe a laser had been involved. I briefly glanced up at her, she still had that trademarked evil grin of hers plastered on her face, like she knew what I was thinking with the evidence before me. Which was about to be spread before me as she rested her perk buttocks against the frame at the foot of the bed, hands out to one side, lightly touching the pair of bed knobs that made up the framework.

I planted a kiss on those inviting lips, they tasted perfectly clean, like she’d had a shower beforehand. I heard her moan in appreciation as I planted another light kiss on them, then another and another. I looked up again, her mouth was slightly hanging open, as if she was close to orgasm already. If that was true, this was the fastest I’d ever known a woman cum from any ministrations like this. She was fiddling with her shirt, trying to unbutton it with one hand while the other was propping her up, grabbing onto one of the giant bed knobs at the foot of the bed.